# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1058500'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
_cell_length_a                   5.8652(5)
_cell_length_b                   9.6315(8)
_cell_length_c                   34.423(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.403(7)
_cell_angle_gamma                90
_cell_volume                     1938.8(3)
_cell_measurement_reflns_used    2727
_cell_measurement_theta_min      4.2647
_cell_measurement_theta_max      29.0188
_cell_oxdiff_length_a            5.8664(3)
_cell_oxdiff_length_b            9.6285(5)
_cell_oxdiff_length_c            34.4250(19)
_cell_oxdiff_angle_alpha         90.048(5)
_cell_oxdiff_angle_beta          94.371(4)
_cell_oxdiff_angle_gamma         90.015(4)
_cell_oxdiff_volume              1938.84(18)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C22 H29 N O2'
_chemical_formula_moiety         'C22 H29 N O2'
_chemical_compound_source        ?
_chemical_formula_weight         339.46


_cell_measurement_temperature    175

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.450
_exptl_absorpt_correction_T_min  0.73703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.73
_montpellier_reflns_completeness_maxres 89.99
_montpellier_reflns_redundancy_maxres 3.47

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.64 4.8 56.60 0.024 94.4 94.44
1 1.64 1.31 4.6 16.64 0.059 100.0 97.14
2 1.31 1.14 4.3 16.37 0.063 100.0 98.08
3 1.14 1.03 3.9 9.92 0.080 100.0 98.55
4 1.03 0.96 3.6 7.52 0.104 100.0 98.84
5 0.96 0.90 3.4 4.93 0.158 100.0 99.03
6 0.90 0.85 3.2 4.21 0.184 100.0 99.17
7 0.85 0.82 2.9 3.67 0.205 100.0 99.27
8 0.82 0.79 2.4 3.00 0.270 97.6 99.08
9 0.79 0.73 1.5 2.14 0.284 49.5 89.99
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      0.0283560000
_diffrn_orient_matrix_UB_12      -0.0396967000
_diffrn_orient_matrix_UB_13      0.0170325000
_diffrn_orient_matrix_UB_21      -0.0168510000
_diffrn_orient_matrix_UB_22      -0.0620520000
_diffrn_orient_matrix_UB_23      -0.0109643000
_diffrn_orient_matrix_UB_31      0.1166882000
_diffrn_orient_matrix_UB_32      0.0007101000
_diffrn_orient_matrix_UB_33      -0.0040857000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -8.00   83.00   1.0000   54.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9412   77.0000  -30.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   48.00   1.0000   54.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9412  -77.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega   42.00   74.00   1.0000   54.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9412  179.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -39.00   43.00   1.0000   54.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7224   38.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega  -48.00   38.00   1.0000   54.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7224   77.0000   60.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega  -33.00   -8.00   1.0000   54.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7224  112.0000 -166.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -29.00    9.00   1.0000   54.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7224  -77.0000   90.0000 38

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            16548
_reflns_number_total             4674
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_unetI/netI     0.0746
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 4674
# Theoretical number of reflections is about 10392


_diffrn_reflns_theta_min         4.273
_diffrn_reflns_theta_max         29.083
_diffrn_measured_fraction_theta_max 0.902

_diffrn_reflns_theta_full        25.011
_diffrn_measured_fraction_theta_full 0.977


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              46

_oxford_diffrn_Wilson_B_factor   2.25
_oxford_diffrn_Wilson_scale      0.04

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.31
_refine_diff_density_max         0.33


# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold


# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_number_parameters     226
_oxford_refine_ls_R_factor_ref   0.0739
_refine_ls_wR_factor_ref         0.0467
_refine_ls_goodness_of_fit_ref   1.1624
_refine_ls_shift/su_max          0.0007419
_refine_ls_shift/su_mean         0.0000736


# The values computed with all filters except I/sigma
_oxford_reflns_number_all        4674
_refine_ls_R_factor_all          0.1074
_refine_ls_wR_factor_all         0.0518

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3363
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_gt          0.0467

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 33.8 30.0 33.4 18.2 3.42 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_...
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.78394(17) 0.40439(10) 0.20572(3) 0.0347 1.0000 Uani . . . . . .
C2 C 0.9362(2) 0.28991(14) 0.20492(4) 0.0344 1.0000 Uani . . . . . .
H21 H 1.0080 0.2955 0.1811 0.0513 1.0000 Uiso R . . . . .
H23 H 1.0495 0.2917 0.2265 0.0515 1.0000 Uiso R . . . . .
H22 H 0.8522 0.2031 0.2053 0.0516 1.0000 Uiso R . . . . .
C3 C 0.6406(2) 0.40520(13) 0.23512(4) 0.0267 1.0000 Uani . . . . . .
C4 C 0.6624(2) 0.32255(13) 0.26792(4) 0.0267 1.0000 Uani . . . . . .
C5 C 0.5001(2) 0.33015(13) 0.29590(4) 0.0254 1.0000 Uani . . . . . .
C6 C 0.3169(2) 0.42125(14) 0.28969(4) 0.0296 1.0000 Uani . . . . . .
C7 C 0.2970(2) 0.50585(14) 0.25702(4) 0.0305 1.0000 Uani . . . . . .
C8 C 0.4573(2) 0.50042(12) 0.22969(4) 0.0249 1.0000 Uani . . . . . .
O9 O 0.43499(16) 0.58360(10) 0.19804(3) 0.0326 1.0000 Uani . . . . . .
H91 H 0.5599 0.5926 0.1874 0.0498 1.0000 Uiso R . . . . .
H71 H 0.1735 0.5665 0.2533 0.0384 1.0000 Uiso R . . . . .
H61 H 0.2035 0.4238 0.3076 0.0369 1.0000 Uiso R . . . . .
C10 C 0.5179(2) 0.24483(14) 0.33088(4) 0.0272 1.0000 Uani . . . . . .
N11 N 0.68455(19) 0.16432(11) 0.34096(3) 0.0271 1.0000 Uani . . . . . .
C12 C 0.6715(2) 0.08402(13) 0.37543(3) 0.0261 1.0000 Uani . . . . . .
C13 C 0.4768(2) 0.00943(14) 0.38306(3) 0.0295 1.0000 Uani . . . . . .
C14 C 0.4739(2) -0.06868(14) 0.41695(4) 0.0303 1.0000 Uani . . . . . .
C15 C 0.6605(2) -0.07558(14) 0.44394(4) 0.0291 1.0000 Uani . . . . . .
C16 C 0.6621(2) -0.15804(16) 0.48145(4) 0.0368 1.0000 Uani . . . . . .
C17 C 0.4479(2) -0.23851(15) 0.48891(4) 0.0316 1.0000 Uani . . . . . .
C18 C 0.4690(3) -0.31065(16) 0.52864(4) 0.0343 1.0000 Uani . . . . . .
C19 C 0.2577(3) -0.39228(16) 0.53770(4) 0.0376 1.0000 Uani . . . . . .
C20 C 0.2821(3) -0.45851(15) 0.57771(4) 0.0359 1.0000 Uani . . . . . .
C21 C 0.0787(3) -0.54025(17) 0.58930(4) 0.0417 1.0000 Uani . . . . . .
C22 C 0.1091(3) -0.5967(2) 0.63016(5) 0.0498 1.0000 Uani . . . . . .
C23 C -0.0840(3) -0.6850(2) 0.64230(5) 0.0547 1.0000 Uani . . . . . .
H231 H -0.0615 -0.7102 0.6698 0.0826 1.0000 Uiso R . . . . .
H232 H -0.2278 -0.6354 0.6379 0.0831 1.0000 Uiso R . . . . .
H233 H -0.0909 -0.7686 0.6270 0.0837 1.0000 Uiso R . . . . .
H221 H 0.1301 -0.5193 0.6484 0.0601 1.0000 Uiso R . . . . .
H222 H 0.2488 -0.6523 0.6319 0.0603 1.0000 Uiso R . . . . .
H211 H -0.0525 -0.4783 0.5877 0.0505 1.0000 Uiso R . . . . .
H212 H 0.0468 -0.6165 0.5713 0.0522 1.0000 Uiso R . . . . .
H201 H 0.3150 -0.3848 0.5972 0.0450 1.0000 Uiso R . . . . .
H202 H 0.4112 -0.5228 0.5779 0.0448 1.0000 Uiso R . . . . .
H192 H 0.1273 -0.3292 0.5367 0.0454 1.0000 Uiso R . . . . .
H191 H 0.2296 -0.4646 0.5184 0.0449 1.0000 Uiso R . . . . .
H181 H 0.5014 -0.2408 0.5488 0.0422 1.0000 Uiso R . . . . .
H182 H 0.5974 -0.3743 0.5290 0.0422 1.0000 Uiso R . . . . .
H172 H 0.3202 -0.1737 0.4888 0.0393 1.0000 Uiso R . . . . .
H171 H 0.4183 -0.3081 0.4682 0.0404 1.0000 Uiso R . . . . .
H161 H 0.6910 -0.0919 0.5031 0.0448 1.0000 Uiso R . . . . .
H162 H 0.7895 -0.2220 0.4821 0.0447 1.0000 Uiso R . . . . .
C24 C 0.8558(2) -0.00173(15) 0.43559(4) 0.0340 1.0000 Uani . . . . . .
C25 C 0.8627(2) 0.07589(15) 0.40182(4) 0.0325 1.0000 Uani . . . . . .
H251 H 0.9970 0.1236 0.3964 0.0399 1.0000 Uiso R . . . . .
H241 H 0.9856 -0.0053 0.4532 0.0416 1.0000 Uiso R . . . . .
H141 H 0.3406 -0.1189 0.4214 0.0363 1.0000 Uiso R . . . . .
H131 H 0.3462 0.0111 0.3649 0.0371 1.0000 Uiso R . . . . .
H101 H 0.3944 0.2489 0.3469 0.0324 1.0000 Uiso R . . . . .
H41 H 0.7823 0.2610 0.2712 0.0345 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.427(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.4206(16) yes
O1 . C3 . 1.3645(15) yes
C2 . H21 . 0.951 no
C2 . H23 . 0.958 no
C2 . H22 . 0.971 no
C3 . C4 . 1.3796(19) yes
C3 . C8 . 1.4144(17) yes
C4 . C5 . 1.4069(18) yes
C4 . H41 . 0.920 no
C5 . C6 . 1.3912(19) yes
C5 . C10 . 1.4547(18) yes
C6 . C7 . 1.3862(19) yes
C6 . H61 . 0.942 no
C7 . C8 . 1.3813(19) yes
C7 . H71 . 0.932 no
C8 . O9 . 1.3505(15) yes
O9 . H91 . 0.849 no
C10 . N11 . 1.2747(18) yes
C10 . H101 . 0.945 no
N11 . C12 . 1.4234(16) yes
C12 . C13 . 1.3912(18) yes
C12 . C25 . 1.3900(19) yes
C13 . C14 . 1.3896(18) yes
C13 . H131 . 0.951 no
C14 . C15 . 1.3818(18) yes
C14 . H141 . 0.942 no
C15 . C16 . 1.5154(18) yes
C15 . C24 . 1.3971(19) yes
C16 . C17 . 1.515(2) yes
C16 . H161 . 0.985 no
C16 . H162 . 0.968 no
C17 . C18 . 1.5304(18) yes
C17 . H172 . 0.974 no
C17 . H171 . 0.985 no
C18 . C19 . 1.520(2) yes
C18 . H181 . 0.976 no
C18 . H182 . 0.970 no
C19 . C20 . 1.5148(19) yes
C19 . H192 . 0.976 no
C19 . H191 . 0.968 no
C20 . C21 . 1.508(2) yes
C20 . H201 . 0.986 no
C20 . H202 . 0.978 no
C21 . C22 . 1.506(2) yes
C21 . H211 . 0.972 no
C21 . H212 . 0.970 no
C22 . C23 . 1.501(2) yes
C22 . H221 . 0.976 no
C22 . H222 . 0.977 no
C23 . H231 . 0.976 no
C23 . H232 . 0.971 no
C23 . H233 . 0.962 no
C24 . C25 . 1.385(2) yes
C24 . H241 . 0.937 no
C25 . H251 . 0.943 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C3 . 116.30(10) yes
O1 . C2 . H21 . 107.1 no
O1 . C2 . H23 . 111.8 no
H21 . C2 . H23 . 109.9 no
O1 . C2 . H22 . 110.3 no
H21 . C2 . H22 . 108.5 no
H23 . C2 . H22 . 109.1 no
O1 . C3 . C4 . 125.46(12) yes
O1 . C3 . C8 . 114.27(11) yes
C4 . C3 . C8 . 120.27(11) yes
C3 . C4 . C5 . 120.35(12) yes
C3 . C4 . H41 . 119.6 no
C5 . C4 . H41 . 120.1 no
C4 . C5 . C6 . 118.86(12) yes
C4 . C5 . C10 . 121.86(12) yes
C6 . C5 . C10 . 119.28(12) yes
C5 . C6 . C7 . 120.75(12) yes
C5 . C6 . H61 . 119.4 no
C7 . C6 . H61 . 119.8 no
C6 . C7 . C8 . 120.74(12) yes
C6 . C7 . H71 . 119.7 no
C8 . C7 . H71 . 119.5 no
C3 . C8 . C7 . 118.99(12) yes
C3 . C8 . O9 . 121.13(11) yes
C7 . C8 . O9 . 119.88(11) yes
C8 . O9 . H91 . 112.1 no
C5 . C10 . N11 . 125.02(12) yes
C5 . C10 . H101 . 116.7 no
N11 . C10 . H101 . 118.2 no
C10 . N11 . C12 . 117.94(11) yes
N11 . C12 . C13 . 122.36(11) yes
N11 . C12 . C25 . 118.90(11) yes
C13 . C12 . C25 . 118.71(12) yes
C12 . C13 . C14 . 120.08(12) yes
C12 . C13 . H131 . 119.9 no
C14 . C13 . H131 . 120.0 no
C13 . C14 . C15 . 122.03(13) yes
C13 . C14 . H141 . 118.6 no
C15 . C14 . H141 . 119.4 no
C14 . C15 . C16 . 123.43(13) yes
C14 . C15 . C24 . 117.19(12) yes
C16 . C15 . C24 . 119.37(12) yes
C15 . C16 . C17 . 117.48(12) yes
C15 . C16 . H161 . 107.1 no
C17 . C16 . H161 . 107.5 no
C15 . C16 . H162 . 107.9 no
C17 . C16 . H162 . 108.6 no
H161 . C16 . H162 . 107.9 no
C16 . C17 . C18 . 111.86(11) yes
C16 . C17 . H172 . 108.6 no
C18 . C17 . H172 . 107.6 no
C16 . C17 . H171 . 109.1 no
C18 . C17 . H171 . 109.6 no
H172 . C17 . H171 . 110.0 no
C17 . C18 . C19 . 114.01(12) yes
C17 . C18 . H181 . 108.8 no
C19 . C18 . H181 . 109.1 no
C17 . C18 . H182 . 107.9 no
C19 . C18 . H182 . 108.4 no
H181 . C18 . H182 . 108.5 no
C18 . C19 . C20 . 112.52(13) yes
C18 . C19 . H192 . 108.7 no
C20 . C19 . H192 . 108.3 no
C18 . C19 . H191 . 109.3 no
C20 . C19 . H191 . 108.7 no
H192 . C19 . H191 . 109.4 no
C19 . C20 . C21 . 116.03(13) yes
C19 . C20 . H201 . 108.4 no
C21 . C20 . H201 . 108.3 no
C19 . C20 . H202 . 106.9 no
C21 . C20 . H202 . 107.2 no
H201 . C20 . H202 . 110.0 no
C20 . C21 . C22 . 113.34(13) yes
C20 . C21 . H211 . 107.7 no
C22 . C21 . H211 . 108.0 no
C20 . C21 . H212 . 110.1 no
C22 . C21 . H212 . 109.1 no
H211 . C21 . H212 . 108.4 no
C21 . C22 . C23 . 115.28(15) yes
C21 . C22 . H221 . 108.9 no
C23 . C22 . H221 . 108.3 no
C21 . C22 . H222 . 107.1 no
C23 . C22 . H222 . 108.7 no
H221 . C22 . H222 . 108.4 no
C22 . C23 . H231 . 111.2 no
C22 . C23 . H232 . 110.1 no
H231 . C23 . H232 . 108.9 no
C22 . C23 . H233 . 108.9 no
H231 . C23 . H233 . 108.6 no
H232 . C23 . H233 . 109.1 no
C15 . C24 . C25 . 121.64(12) yes
C15 . C24 . H241 . 119.1 no
C25 . C24 . H241 . 119.2 no
C12 . C25 . C24 . 120.33(12) yes
C12 . C25 . H251 . 119.2 no
C24 . C25 . H251 . 120.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O9 . H91 . N11 4_655 164.21(4) 0.849 1.975 2.801(2) yes
C4 . H41 . O9 4_645 161.35(4) 0.920 2.554 3.438(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/04/14 at 15:52:08
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  23,X'S) H   (  22,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE O   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S)
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 172,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 192,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/04/14 at 15:52:08
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1058501'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
_cell_length_a                   9.1728(5)
_cell_length_b                   13.3311(5)
_cell_length_c                   13.1709(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.107(5)
_cell_angle_gamma                90
_cell_volume                     1539.33(13)
_cell_measurement_reflns_used    5568
_cell_measurement_theta_min      4.4171
_cell_measurement_theta_max      37.4711
_cell_oxdiff_length_a            9.1732(3)
_cell_oxdiff_length_b            13.3316(5)
_cell_oxdiff_length_c            13.1691(5)
_cell_oxdiff_angle_alpha         90.003(3)
_cell_oxdiff_angle_beta          107.096(3)
_cell_oxdiff_angle_gamma         90.044(3)
_cell_oxdiff_volume              1539.33(10)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C18 H21 N O2'
_chemical_formula_moiety         'C18 H21 N O2'
_chemical_compound_source        ?
_chemical_formula_weight         283.36


_cell_measurement_temperature    175

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.300
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_max          0.550
_exptl_absorpt_correction_T_min  0.99460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             608.000
_exptl_absorpt_coefficient_mu    0.079
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.58
_montpellier_reflns_completeness_maxres 96.63
_montpellier_reflns_redundancy_maxres 5.66

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.28 7.9 61.32 0.019 98.0 97.95
1 1.28 1.01 7.9 26.00 0.043 100.0 98.97
2 1.01 0.89 6.9 13.22 0.087 100.0 99.31
3 0.88 0.80 6.2 8.22 0.153 100.0 99.48
4 0.80 0.74 5.7 6.95 0.179 100.0 99.58
5 0.74 0.70 5.3 6.01 0.202 100.0 99.65
6 0.70 0.66 4.9 5.14 0.237 100.0 99.70
7 0.66 0.64 4.5 4.08 0.288 100.0 99.74
8 0.64 0.61 4.3 3.88 0.310 100.0 99.77
9 0.61 0.58 3.0 3.28 0.329 75.4 96.63
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      0.0065128000
_diffrn_orient_matrix_UB_12      0.0219029000
_diffrn_orient_matrix_UB_13      -0.0475599000
_diffrn_orient_matrix_UB_21      -0.0049570000
_diffrn_orient_matrix_UB_22      0.0484705000
_diffrn_orient_matrix_UB_23      0.0209443000
_diffrn_orient_matrix_UB_31      0.0804830000
_diffrn_orient_matrix_UB_32      0.0012568000
_diffrn_orient_matrix_UB_33      0.0217900000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   48.00  113.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -       38.0125  179.0000  -30.0000 65

#__ type_ start__ end____ width___ exp.time_
  2 omega  -29.00   -3.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -       38.0125  -38.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   10.00  105.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -       38.0125   77.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
  4 omega  -35.00  104.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -       38.0125    0.0000  -90.0000 139

#__ type_ start__ end____ width___ exp.time_
  5 omega   30.00   57.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -       38.0125  -38.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -92.00  -60.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -      -38.7938  179.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  7 omega  -81.00  -53.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -      -38.7938  179.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
  8 omega  -89.00  -30.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -      -38.7938  139.0000  -35.0000 59

#__ type_ start__ end____ width___ exp.time_
  9 omega -104.00  -75.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -      -38.7938  139.0000   96.0000 29

#__ type_ start__ end____ width___ exp.time_
 10 omega -115.00  -62.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -      -38.7938  179.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega    8.00  108.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -       38.0125   77.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 12 omega    8.00  108.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -       38.0125   77.0000 -150.0000 100

#__ type_ start__ end____ width___ exp.time_
 13 omega  -34.00    2.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -       38.0125  -38.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
 14 omega   13.00  110.00   1.0000   12.1000
omega____ theta____ kappa____ phi______ frames
    -       38.0125   38.0000  -30.0000 97

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            45278
_reflns_number_total             7870
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_unetI/netI     0.1572
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 7870
# Theoretical number of reflections is about 7145


_diffrn_reflns_theta_min         4.426
_diffrn_reflns_theta_max         37.560
_diffrn_measured_fraction_theta_max 0.966

_diffrn_reflns_theta_full        34.931
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -15
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              22
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   1.17
_oxford_diffrn_Wilson_scale      0.06

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.46


# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold


# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     28
_refine_ls_number_parameters     218
_oxford_refine_ls_R_factor_ref   0.0629
_refine_ls_wR_factor_ref         0.0599
_refine_ls_goodness_of_fit_ref   0.9423
_refine_ls_shift/su_max          0.0078854
_refine_ls_shift/su_mean         0.0004914


# The values computed with all filters except I/sigma
_oxford_reflns_number_all        3552
_refine_ls_R_factor_all          0.0719
_refine_ls_wR_factor_all         0.0609

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3132
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_gt          0.0599

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
 Method = Robust Weighting (Prince, 1982)
 W = [weight] * [1-(deltaF/6*sigmaF)²]²
 Ai are:
 40.9 51.8 43.8 20.5 4.83
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_...
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.83685(12) 0.26407(7) 1.00924(7) 0.0278 1.0000 Uani . . . . . .
C2 C 0.83750(13) 0.31402(9) 0.91986(8) 0.0202 1.0000 Uani . . . . . .
C3 C 0.83001(13) 0.26219(8) 0.82502(9) 0.0190 1.0000 Uani . . . . . .
O4 O 0.82841(12) 0.16056(7) 0.83414(7) 0.0273 1.0000 Uani . . . . . .
C5 C 0.82603(18) 0.10323(10) 0.74216(10) 0.0299 1.0000 Uani . . . . . .
H53 H 0.8343 0.0352 0.7657 0.0427 1.0000 Uiso R . . . . .
H52 H 0.9111 0.1204 0.7150 0.0418 1.0000 Uiso R . . . . .
H51 H 0.7317 0.1134 0.6892 0.0424 1.0000 Uiso R . . . . .
C6 C 0.82345(14) 0.31464(9) 0.73324(9) 0.0203 1.0000 Uani . . . . . .
C7 C 0.82934(13) 0.42024(9) 0.73500(9) 0.0202 1.0000 Uani . . . . . .
C8 C 0.80580(14) 0.47947(9) 0.63793(9) 0.0212 1.0000 Uani . . . . . .
N9 N 0.77286(12) 0.44348(7) 0.54386(8) 0.0207 1.0000 Uani . . . . . .
C10 C 0.74184(13) 0.51557(9) 0.45959(9) 0.0195 1.0000 Uani . . . . . .
C11 C 0.84315(14) 0.59211(9) 0.45580(9) 0.0216 1.0000 Uani . . . . . .
C12 C 0.80511(15) 0.66243(9) 0.37366(10) 0.0246 1.0000 Uani . . . . . .
C13 C 0.66553(15) 0.65784(10) 0.29434(10) 0.0252 1.0000 Uani . . . . . .
C14 C 0.56666(15) 0.57908(10) 0.29785(11) 0.0281 1.0000 Uani . . . . . .
C15 C 0.60427(14) 0.50815(10) 0.37879(10) 0.0262 1.0000 Uani . . . . . .
H151 H 0.5347 0.4553 0.3785 0.0300 1.0000 Uiso R . . . . .
H141 H 0.4709 0.5750 0.2449 0.0325 1.0000 Uiso R . . . . .
C16 C 0.62167(18) 0.73684(10) 0.20747(11) 0.0351 1.0000 Uani D . . . . .
C17 C 0.72116(18) 0.73451(10) 0.13105(12) 0.0347 0.914(4) Uani D U P 1 1 .
C18 C 0.70732(18) 0.64245(11) 0.06200(13) 0.0388 0.914(4) Uani D U P 1 1 .
C19 C 0.5572(3) 0.63294(15) -0.02417(16) 0.0525 0.914(4) Uani D U P 1 1 .
H121 H 0.8749 0.7129 0.3736 0.0288 1.0000 Uiso R . . . . .
H111 H 0.9359 0.5961 0.5074 0.0253 1.0000 Uiso R . . . . .
H81 H 0.8143 0.5504 0.6477 0.0238 1.0000 Uiso R . . . . .
C20 C 0.84328(15) 0.47042(9) 0.83031(9) 0.0236 1.0000 Uani . . . . . .
C21 C 0.84698(15) 0.41779(9) 0.92216(9) 0.0234 1.0000 Uani . . . . . .
H211 H 0.8553 0.4500 0.9862 0.0254 1.0000 Uiso R . . . . .
H201 H 0.8467 0.5411 0.8320 0.0270 1.0000 Uiso R . . . . .
H61 H 0.8182 0.2804 0.6719 0.0235 1.0000 Uiso R . . . . .
H11 H 0.8091 0.2053 1.0000 0.0403 1.0000 Uiso R . . . . .
C181 C 0.588(2) 0.6277(10) 0.0433(10) 0.0490 0.086(4) Uani D U P 1 2 .
C171 C 0.653(2) 0.7205(10) 0.1024(9) 0.0480 0.086(4) Uani D U P 1 2 .
C191 C 0.615(3) 0.6173(15) -0.0631(11) 0.0541 0.086(4) Uani D U P 1 2 .
H171 H 0.8248 0.7409 0.1723 0.0437 0.914(4) Uiso R . P 1 1 .
H172 H 0.6930 0.7906 0.0850 0.0437 0.914(4) Uiso R . P 1 1 .
H1711 H 0.7390 0.7500 0.0884 0.0586 0.086(4) Uiso R . P 1 2 .
H1712 H 0.5638 0.7576 0.0672 0.0586 0.086(4) Uiso R . P 1 2 .
H181 H 0.7867 0.6445 0.0292 0.0482 0.914(4) Uiso R . P 1 1 .
H182 H 0.7197 0.5849 0.1063 0.0482 0.914(4) Uiso R . P 1 1 .
H1811 H 0.6535 0.5834 0.0929 0.0585 0.086(4) Uiso R . P 1 2 .
H1812 H 0.4852 0.6075 0.0313 0.0585 0.086(4) Uiso R . P 1 2 .
H191 H 0.5567 0.5736 -0.0642 0.0679 0.914(4) Uiso R . P 1 1 .
H192 H 0.5435 0.6896 -0.0697 0.0679 0.914(4) Uiso R . P 1 1 .
H193 H 0.4766 0.6301 0.0075 0.0679 0.914(4) Uiso R . P 1 1 .
H1911 H 0.6010 0.5502 -0.0885 0.0589 0.086(4) Uiso R . P 1 2 .
H1912 H 0.7181 0.6366 -0.0522 0.0589 0.086(4) Uiso R . P 1 2 .
H1913 H 0.5498 0.6607 -0.1138 0.0589 0.086(4) Uiso R . P 1 2 .
H161 H 0.6328 0.8010 0.2403 0.0408 0.914(4) Uiso R . P 1 1 .
H162 H 0.5181 0.7269 0.1676 0.0408 0.914(4) Uiso R . P 1 1 .
H163 H 0.6985 0.7866 0.2304 0.0408 0.086(4) Uiso R . P 1 2 .
H164 H 0.5272 0.7625 0.2121 0.0408 0.086(4) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.299(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.3541(14) yes
O1 . H11 . 0.822 no
C2 . C3 . 1.4113(15) yes
C2 . C21 . 1.3859(17) yes
C3 . O4 . 1.3606(14) yes
C3 . C6 . 1.3824(15) yes
O4 . C5 . 1.4271(14) yes
C5 . H53 . 0.954 no
C5 . H52 . 0.976 no
C5 . H51 . 0.948 no
C6 . C7 . 1.4087(16) yes
C6 . H61 . 0.917 no
C7 . C8 . 1.4636(15) yes
C7 . C20 . 1.3946(16) yes
C8 . N9 . 1.2793(16) yes
C8 . H81 . 0.955 no
N9 . C10 . 1.4320(14) yes
C10 . C11 . 1.3909(17) yes
C10 . C15 . 1.3945(17) yes
C11 . C12 . 1.3960(16) yes
C11 . H111 . 0.921 no
C12 . C13 . 1.3955(19) yes
C12 . H121 . 0.929 no
C13 . C14 . 1.3970(18) yes
C13 . C16 . 1.5197(17) yes
C14 . C15 . 1.3904(17) yes
C14 . H141 . 0.949 no
C15 . H151 . 0.950 no
C16 . C17 . 1.545(2) yes
C16 . H161 . 0.950 no
C16 . H162 . 0.950 no
C16 . C171 . 1.508(5) yes
C16 . H163 . 0.950 no
C16 . H164 . 0.950 no
C17 . C18 . 1.510(2) yes
C17 . H171 . 0.950 no
C17 . H172 . 0.950 no
C18 . C19 . 1.511(2) yes
C18 . H181 . 0.950 no
C18 . H182 . 0.950 no
C19 . H191 . 0.950 no
C19 . H192 . 0.950 no
C19 . H193 . 0.950 no
C20 . C21 . 1.3902(16) yes
C20 . H201 . 0.943 no
C21 . H211 . 0.929 no
C181 . C171 . 1.488(5) yes
C181 . C191 . 1.499(5) yes
C181 . H1811 . 0.950 no
C181 . H1812 . 0.950 no
C171 . H1711 . 0.950 no
C171 . H1712 . 0.950 no
C191 . H1911 . 0.950 no
C191 . H1912 . 0.950 no
C191 . H1913 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . H11 . 114.9 no
O1 . C2 . C3 . 121.14(11) yes
O1 . C2 . C21 . 119.22(10) yes
C3 . C2 . C21 . 119.63(10) yes
C2 . C3 . O4 . 114.10(10) yes
C2 . C3 . C6 . 120.31(11) yes
O4 . C3 . C6 . 125.59(10) yes
C3 . O4 . C5 . 117.14(9) yes
O4 . C5 . H53 . 104.7 no
O4 . C5 . H52 . 111.8 no
H53 . C5 . H52 . 110.2 no
O4 . C5 . H51 . 109.3 no
H53 . C5 . H51 . 110.1 no
H52 . C5 . H51 . 110.6 no
C3 . C6 . C7 . 119.96(10) yes
C3 . C6 . H61 . 119.7 no
C7 . C6 . H61 . 120.3 no
C6 . C7 . C8 . 121.98(10) yes
C6 . C7 . C20 . 119.15(10) yes
C8 . C7 . C20 . 118.58(10) yes
C7 . C8 . N9 . 125.16(11) yes
C7 . C8 . H81 . 115.6 no
N9 . C8 . H81 . 119.3 no
C8 . N9 . C10 . 115.81(10) yes
N9 . C10 . C11 . 122.52(10) yes
N9 . C10 . C15 . 118.21(10) yes
C11 . C10 . C15 . 119.27(11) yes
C10 . C11 . C12 . 120.20(11) yes
C10 . C11 . H111 . 119.8 no
C12 . C11 . H111 . 120.0 no
C11 . C12 . C13 . 121.05(11) yes
C11 . C12 . H121 . 118.1 no
C13 . C12 . H121 . 120.8 no
C12 . C13 . C14 . 118.02(11) yes
C12 . C13 . C16 . 120.97(12) yes
C14 . C13 . C16 . 121.00(12) yes
C13 . C14 . C15 . 121.29(12) yes
C13 . C14 . H141 . 119.2 no
C15 . C14 . H141 . 119.5 no
C10 . C15 . C14 . 120.10(11) yes
C10 . C15 . H151 . 120.8 no
C14 . C15 . H151 . 119.1 no
C13 . C16 . C17 . 113.59(12) yes
C13 . C16 . H161 . 108.2 no
C17 . C16 . H161 . 108.1 no
C13 . C16 . H162 . 108.7 no
C17 . C16 . H162 . 108.8 no
H161 . C16 . H162 . 109.5 no
C13 . C16 . C171 . 120.7(8) yes
C13 . C16 . H163 . 103.7 no
C171 . C16 . H163 . 94.1 no
C13 . C16 . H164 . 104.2 no
C171 . C16 . H164 . 122.2 no
H163 . C16 . H164 . 109.5 no
C16 . C17 . C18 . 116.58(5) yes
C16 . C17 . H171 . 108.0 no
C18 . C17 . H171 . 108.0 no
C16 . C17 . H172 . 107.4 no
C18 . C17 . H172 . 107.2 no
H171 . C17 . H172 . 109.5 no
C17 . C18 . C19 . 114.66(5) yes
C17 . C18 . H181 . 108.1 no
C19 . C18 . H181 . 108.2 no
C17 . C18 . H182 . 108.2 no
C19 . C18 . H182 . 108.2 no
H181 . C18 . H182 . 109.5 no
C18 . C19 . H191 . 110.0 no
C18 . C19 . H192 . 109.2 no
H191 . C19 . H192 . 109.5 no
C18 . C19 . H193 . 109.2 no
H191 . C19 . H193 . 109.5 no
H192 . C19 . H193 . 109.5 no
C7 . C20 . C21 . 120.89(11) yes
C7 . C20 . H201 . 119.7 no
C21 . C20 . H201 . 119.4 no
C20 . C21 . C2 . 119.96(10) yes
C20 . C21 . H211 . 122.1 no
C2 . C21 . H211 . 118.0 no
C171 . C181 . C191 . 114.64(5) yes
C171 . C181 . H1811 . 94.8 no
C191 . C181 . H1811 . 110.0 no
C171 . C181 . H1812 . 123.1 no
C191 . C181 . H1812 . 104.2 no
H1811 . C181 . H1812 . 109.5 no
C16 . C171 . C181 . 116.56(5) yes
C16 . C171 . H1711 . 120.8 no
C181 . C171 . H1711 . 117.9 no
C16 . C171 . H1712 . 90.4 no
C181 . C171 . H1712 . 91.5 no
H1711 . C171 . H1712 . 109.5 no
C181 . C191 . H1911 . 112.0 no
C181 . C191 . H1912 . 105.3 no
H1911 . C191 . H1912 . 109.5 no
C181 . C191 . H1913 . 111.1 no
H1911 . C191 . H1913 . 109.5 no
H1912 . C191 . H1913 . 109.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H61 . O1 3_554 163.63(4) 0.917 2.277 3.168(5) yes
O1 . H11 . N9 3_555 156.69(4) 0.822 2.119 2.892(5) yes


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1058502'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
_cell_length_a                   4.6306(8)
_cell_length_b                   8.8802(17)
_cell_length_c                   23.893(3)
_cell_angle_alpha                95.744(13)
_cell_angle_beta                 91.859(12)
_cell_angle_gamma                101.739(15)
_cell_volume                     955.71(11)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C15 H20 N3 O3 
# Dc =      1.51 Fooo =    380.00 Mu =      1.07 M =    435.51
# Found Formula = C14 H17.33 N1.33 O2 
# Dc =      1.23 FOOO =    380.00 Mu =      0.83 M =    354.45

_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_compound_source        ?
_chemical_formula_weight         354.44


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    175

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_max          0.250

_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.083

# Sheldrick geometric approximatio 0.99 1.00
_exptl_absorpt_correction_type   multi-scan

_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector_area_resol_mean 16.1593

_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       1.08
_montpellier_reflns_completeness_maxres 90.89
_montpellier_reflns_redundancy_maxres 1.67

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.75 2.2 16.39 0.043 96.0 95.99
1 1.75 1.38 1.6 4.12 0.120 91.1 93.49
2 1.38 1.20 1.5 2.82 0.102 92.8 93.25
3 1.20 1.08 1.4 2.35 0.099 84.5 90.89
4 1.08 1.00 1.3 1.90 0.143 87.8 90.25
5 1.00 0.94 1.2 1.21 0.275 87.3 89.75
6 0.94 0.88 1.2 0.98 0.421 76.2 87.53
7 0.88 0.84 1.2 0.67 0.635 76.9 86.04
8 0.84 0.81 1.1 0.69 0.548 78.2 85.09
9 0.81 0.73 1.1 0.45 0.488 26.4 69.51
#End reflection statistics
_diffrn_measurement_method       ω
_diffrn_orient_matrix_UB_11      -0.0728331000
_diffrn_orient_matrix_UB_12      0.0560836000
_diffrn_orient_matrix_UB_13      -0.0097944000
_diffrn_orient_matrix_UB_21      0.0476894000
_diffrn_orient_matrix_UB_22      -0.0160152000
_diffrn_orient_matrix_UB_23      -0.0274646000
_diffrn_orient_matrix_UB_31      -0.1302676000
_diffrn_orient_matrix_UB_32      -0.0577369000
_diffrn_orient_matrix_UB_33      -0.0065263000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.5163 4218 2398
2 0.4837 4226 2398
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -23.00   25.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0127  -99.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega   36.00   88.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5908 -178.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   87.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5908   38.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   43.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5908   57.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega  -36.00   64.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5908  -19.0000    0.0000 100

;

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      175
_diffrn_reflns_number            7017
_reflns_number_total             4096
_diffrn_reflns_av_R_equivalents  0.084
_diffrn_reflns_av_unetI/netI     0.078
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 4096
# Theoretical number of reflections is about 10343


_diffrn_reflns_theta_min         1.716
_diffrn_reflns_theta_max         29.184
_diffrn_measured_fraction_theta_max 0.833

_diffrn_reflns_theta_full        25.099
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -5
_reflns_limit_h_max              5
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              -30
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.32
_refine_diff_density_max         0.44


# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         1866
_refine_ls_number_restraints     8
_refine_ls_number_parameters     236
_oxford_refine_ls_R_factor_ref   0.0836
_refine_ls_wR_factor_ref         0.0897
_refine_ls_goodness_of_fit_ref   1.0036
_refine_ls_shift/su_max          0.0000773
_refine_ls_shift/su_mean         0.0000100


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7017
_refine_ls_R_factor_all          0.2757
_refine_ls_wR_factor_all         0.1788

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1686
_refine_ls_R_factor_gt           0.0836
_refine_ls_wR_factor_gt          0.0897

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 16.9 -6.25 14.3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.5409(10) 0.3183(6) 0.30502(18) 0.0400 1.0000 Uani . . . . . .
C2 C 0.6684(15) 0.2977(8) 0.3544(3) 0.0269 1.0000 Uani . U . . . .
C3 C 0.9159(15) 0.4080(8) 0.3768(3) 0.0355 1.0000 Uani . U . . . .
C4 C 1.0561(13) 0.3908(8) 0.4268(3) 0.0308 1.0000 Uani . U . . . .
C5 C 0.9417(14) 0.2672(9) 0.4554(3) 0.0295 1.0000 Uani . U . . . .
N6 N 1.0821(14) 0.2483(8) 0.5086(3) 0.0419 1.0000 Uani . U . . . .
O7 O 1.3204(12) 0.3328(7) 0.5244(2) 0.0524 1.0000 Uani . . . . . .
O8 O 0.9579(13) 0.1471(8) 0.5367(2) 0.0748 1.0000 Uani . . . . . .
C9 C 0.6974(15) 0.1534(8) 0.4340(3) 0.0303 1.0000 Uani . U . . . .
C10 C 0.5572(15) 0.1693(8) 0.3839(3) 0.0244 1.0000 Uani . . . . . .
C11 C 0.3010(15) 0.0528(8) 0.3603(3) 0.0264 1.0000 Uani . . . . . .
N12 N 0.1576(11) 0.0648(7) 0.3153(2) 0.0224 1.0000 Uani . . . . . .
C13 C -0.0922(15) -0.0494(8) 0.2940(3) 0.0233 1.0000 Uani . . . . . .
C14 C -0.2188(14) -0.1766(8) 0.3211(3) 0.0282 1.0000 Uani . . . . . .
C15 C -0.4624(15) -0.2820(9) 0.2947(3) 0.0333 1.0000 Uani . . . . . .
C16 C -0.5852(15) -0.2644(9) 0.2428(3) 0.0306 1.0000 Uani . . . . . .
C17 C -0.8400(13) -0.3875(8) 0.2141(3) 0.0310 1.0000 Uani . . . . . .
C18 C -0.7287(14) -0.5159(8) 0.1805(3) 0.0284 1.0000 Uani . . . . . .
C19 C -0.9771(14) -0.6460(8) 0.1523(3) 0.0276 1.0000 Uani . . . . . .
C20 C -0.8675(13) -0.7838(8) 0.1251(3) 0.0284 1.0000 Uani . . . . . .
C21 C -1.1093(15) -0.9125(8) 0.0959(3) 0.0321 1.0000 Uani . . . . . .
C22 C -1.0059(16) -1.0595(8) 0.0778(3) 0.0373 1.0000 Uani . . . . . .
C23 C -1.2400(16) -1.1941(8) 0.0508(3) 0.0421 1.0000 Uani . . . . . .
C24 C -1.1273(18) -1.3402(9) 0.0341(4) 0.0568 1.0000 Uani . . . . . .
H243 H -1.2837 -1.4208 0.0173 0.0861 1.0000 Uiso R . . . . .
H242 H -1.0439 -1.3747 0.0667 0.0862 1.0000 Uiso R . . . . .
H241 H -0.9764 -1.3183 0.0077 0.0861 1.0000 Uiso R . . . . .
H232 H -1.3956 -1.2191 0.0768 0.0533 1.0000 Uiso R . . . . .
H231 H -1.3192 -1.1610 0.0172 0.0532 1.0000 Uiso R . . . . .
H221 H -0.9226 -1.0935 0.1109 0.0434 1.0000 Uiso R . . . . .
H222 H -0.8523 -1.0377 0.0516 0.0430 1.0000 Uiso R . . . . .
H212 H -1.2670 -0.9361 0.1215 0.0402 1.0000 Uiso R . . . . .
H211 H -1.1866 -0.8762 0.0630 0.0404 1.0000 Uiso R . . . . .
H201 H -0.7641 -0.8274 0.1539 0.0364 1.0000 Uiso R . . . . .
H202 H -0.7292 -0.7461 0.0973 0.0362 1.0000 Uiso R . . . . .
H192 H -1.1144 -0.6837 0.1805 0.0329 1.0000 Uiso R . . . . .
H191 H -1.0795 -0.6018 0.1244 0.0332 1.0000 Uiso R . . . . .
H182 H -0.6083 -0.5628 0.2050 0.0363 1.0000 Uiso R . . . . .
H181 H -0.6076 -0.4715 0.1516 0.0360 1.0000 Uiso R . . . . .
H171 H -0.9664 -0.4328 0.2425 0.0412 1.0000 Uiso R . . . . .
H172 H -0.9553 -0.3397 0.1892 0.0413 1.0000 Uiso R . . . . .
C25 C -0.4602(15) -0.1335(9) 0.2179(3) 0.0359 1.0000 Uani . . . . . .
C26 C -0.2170(15) -0.0287(8) 0.2428(3) 0.0294 1.0000 Uani . . . . . .
H261 H -0.1377 0.0578 0.2249 0.0349 1.0000 Uiso R . . . . .
H251 H -0.5423 -0.1168 0.1839 0.0415 1.0000 Uiso R . . . . .
H151 H -0.5429 -0.3681 0.3131 0.0392 1.0000 Uiso R . . . . .
H141 H -0.1410 -0.1929 0.3559 0.0363 1.0000 Uiso R . . . . .
H111 H 0.2398 -0.0333 0.3796 0.0300 1.0000 Uiso R . . . . .
H91 H 0.6304 0.0707 0.4542 0.0418 1.0000 Uiso R . . . . .
H41 H 1.2241 0.4612 0.4414 0.0371 1.0000 Uiso R . . . . .
H31 H 0.9883 0.4921 0.3569 0.0441 1.0000 Uiso R . . . . .
H11 H 0.4145 0.2381 0.3017 0.0613 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.728(14)

loop_
_oxford_twin_element_scale_factors
0.523(3)
0.477(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.348(8) yes
O1 . H11 . 0.820 no
C2 . C3 . 1.400(9) yes
C2 . C10 . 1.417(9) yes
C3 . C4 . 1.377(10) yes
C3 . H31 . 0.936 no
C4 . C5 . 1.374(9) yes
C4 . H41 . 0.927 no
C5 . N6 . 1.450(9) yes
C5 . C9 . 1.398(9) yes
N6 . O7 . 1.226(7) yes
N6 . O8 . 1.234(8) yes
C9 . C10 . 1.377(9) yes
C9 . H91 . 0.925 no
C10 . C11 . 1.462(9) yes
C11 . N12 . 1.270(8) yes
C11 . H111 . 0.933 no
N12 . C13 . 1.416(8) yes
C13 . C14 . 1.394(9) yes
C13 . C26 . 1.380(9) yes
C14 . C15 . 1.398(9) yes
C14 . H141 . 0.932 no
C15 . C16 . 1.385(9) yes
C15 . H151 . 0.937 no
C16 . C17 . 1.526(9) yes
C16 . C25 . 1.388(10) yes
C17 . C18 . 1.514(9) yes
C17 . H171 . 0.975 no
C17 . H172 . 0.970 no
C18 . C19 . 1.537(8) yes
C18 . H182 . 0.975 no
C18 . H181 . 0.968 no
C19 . C20 . 1.513(9) yes
C19 . H192 . 0.977 no
C19 . H191 . 0.966 no
C20 . C21 . 1.523(9) yes
C20 . H201 . 0.979 no
C20 . H202 . 0.974 no
C21 . C22 . 1.508(9) yes
C21 . H212 . 0.972 no
C21 . H211 . 0.964 no
C22 . C23 . 1.514(9) yes
C22 . H221 . 0.971 no
C22 . H222 . 0.965 no
C23 . C24 . 1.516(10) yes
C23 . H232 . 0.973 no
C23 . H231 . 0.968 no
C24 . H243 . 0.954 no
C24 . H242 . 0.964 no
C24 . H241 . 0.959 no
C25 . C26 . 1.381(9) yes
C25 . H251 . 0.924 no
C26 . H261 . 0.932 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . H11 . 97.2 no
O1 . C2 . C3 . 118.3(7) yes
O1 . C2 . C10 . 121.8(6) yes
C3 . C2 . C10 . 119.8(7) yes
C2 . C3 . C4 . 120.4(8) yes
C2 . C3 . H31 . 119.1 no
C4 . C3 . H31 . 120.4 no
C3 . C4 . C5 . 119.0(6) yes
C3 . C4 . H41 . 121.1 no
C5 . C4 . H41 . 119.9 no
C4 . C5 . N6 . 120.0(6) yes
C4 . C5 . C9 . 122.3(6) yes
N6 . C5 . C9 . 117.7(7) yes
C5 . N6 . O7 . 119.2(7) yes
C5 . N6 . O8 . 118.9(6) yes
O7 . N6 . O8 . 121.9(6) yes
C5 . C9 . C10 . 119.0(7) yes
C5 . C9 . H91 . 119.6 no
C10 . C9 . H91 . 121.4 no
C2 . C10 . C9 . 119.4(6) yes
C2 . C10 . C11 . 120.0(6) yes
C9 . C10 . C11 . 120.6(7) yes
C10 . C11 . N12 . 123.0(7) yes
C10 . C11 . H111 . 117.9 no
N12 . C11 . H111 . 119.0 no
C11 . N12 . C13 . 121.5(7) yes
N12 . C13 . C14 . 124.9(6) yes
N12 . C13 . C26 . 116.0(7) yes
C14 . C13 . C26 . 119.1(7) yes
C13 . C14 . C15 . 118.8(7) yes
C13 . C14 . H141 . 121.0 no
C15 . C14 . H141 . 120.1 no
C14 . C15 . C16 . 122.6(8) yes
C14 . C15 . H151 . 118.0 no
C16 . C15 . H151 . 119.4 no
C15 . C16 . C17 . 120.6(8) yes
C15 . C16 . C25 . 117.0(7) yes
C17 . C16 . C25 . 122.3(7) yes
C16 . C17 . C18 . 111.4(6) yes
C16 . C17 . H171 . 109.6 no
C18 . C17 . H171 . 108.3 no
C16 . C17 . H172 . 109.2 no
C18 . C17 . H172 . 109.4 no
H171 . C17 . H172 . 109.0 no
C17 . C18 . C19 . 113.6(5) yes
C17 . C18 . H182 . 109.9 no
C19 . C18 . H182 . 107.4 no
C17 . C18 . H181 . 108.3 no
C19 . C18 . H181 . 108.8 no
H182 . C18 . H181 . 108.7 no
C18 . C19 . C20 . 113.6(5) yes
C18 . C19 . H192 . 109.6 no
C20 . C19 . H192 . 107.2 no
C18 . C19 . H191 . 107.0 no
C20 . C19 . H191 . 110.1 no
H192 . C19 . H191 . 109.3 no
C19 . C20 . C21 . 114.4(6) yes
C19 . C20 . H201 . 109.2 no
C21 . C20 . H201 . 108.1 no
C19 . C20 . H202 . 107.3 no
C21 . C20 . H202 . 108.5 no
H201 . C20 . H202 . 109.2 no
C20 . C21 . C22 . 113.8(6) yes
C20 . C21 . H212 . 108.6 no
C22 . C21 . H212 . 108.5 no
C20 . C21 . H211 . 108.6 no
C22 . C21 . H211 . 108.5 no
H212 . C21 . H211 . 108.8 no
C21 . C22 . C23 . 116.2(6) yes
C21 . C22 . H221 . 107.9 no
C23 . C22 . H221 . 107.0 no
C21 . C22 . H222 . 109.0 no
C23 . C22 . H222 . 108.1 no
H221 . C22 . H222 . 108.4 no
C22 . C23 . C24 . 114.4(6) yes
C22 . C23 . H232 . 109.3 no
C24 . C23 . H232 . 107.8 no
C22 . C23 . H231 . 106.9 no
C24 . C23 . H231 . 108.4 no
H232 . C23 . H231 . 109.9 no
C23 . C24 . H243 . 110.8 no
C23 . C24 . H242 . 110.1 no
H243 . C24 . H242 . 108.7 no
C23 . C24 . H241 . 109.0 no
H243 . C24 . H241 . 109.5 no
H242 . C24 . H241 . 108.7 no
C16 . C25 . C26 . 121.4(7) yes
C16 . C25 . H251 . 118.9 no
C26 . C25 . H251 . 119.7 no
C25 . C26 . C13 . 121.0(8) yes
C25 . C26 . H261 . 119.3 no
C13 . C26 . H261 . 119.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C11 . H111 . O8 2_656 150.5(2) 0.933 2.451 3.294(10) yes
C4 . H41 . O7 2_866 175.7(2) 0.927 2.546 3.471(10) yes
O1 . H11 . C11 . 130.7(2) 0.820 2.258 2.862(10) yes
O1 . H11 . N12 . 164.0(2) 0.820 1.808 2.606(10) yes


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8
_database_code_depnum_ccdc_archive 'CCDC 1058503'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_exptl_special_details           
;
 The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
_cell_length_a                   9.6623(3)
_cell_length_b                   13.1399(4)
_cell_length_c                   13.4402(4)
_cell_angle_alpha                96.420(3)
_cell_angle_beta                 103.728(3)
_cell_angle_gamma                92.257(3)
_cell_volume                     1643.42(10)
_cell_measurement_reflns_used    7153
_cell_measurement_theta_min      4.1426
_cell_measurement_theta_max      29.0795
_cell_oxdiff_length_a            9.6623(3)
_cell_oxdiff_length_b            13.1399(4)
_cell_oxdiff_length_c            13.4402(4)
_cell_oxdiff_angle_alpha         96.420(3)
_cell_oxdiff_angle_beta          103.728(3)
_cell_oxdiff_angle_gamma         92.257(3)
_cell_oxdiff_volume              1643.42(9)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C21 H21 N O'
_chemical_formula_moiety         'C21 H21 N O'
_chemical_compound_source        ?
_chemical_formula_weight         303.39


_cell_measurement_temperature    175

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_max          0.400
_exptl_absorpt_correction_T_min  0.95452
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.075
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.73
_montpellier_reflns_completeness_maxres 90.71
_montpellier_reflns_redundancy_maxres 4.57

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.61 7.2 76.18 0.016 96.7 96.74
1 1.61 1.28 6.4 25.76 0.039 100.0 98.34
2 1.28 1.13 5.7 22.82 0.039 100.0 98.89
3 1.13 1.02 5.1 14.07 0.057 100.0 99.16
4 1.02 0.95 4.7 9.62 0.094 100.0 99.33
5 0.95 0.89 4.3 7.18 0.125 100.0 99.44
6 0.89 0.85 4.0 5.88 0.162 100.0 99.52
7 0.85 0.81 3.7 4.67 0.200 100.0 99.58
8 0.81 0.78 2.9 4.17 0.206 97.1 99.30
9 0.78 0.73 1.6 2.65 0.233 51.2 90.71
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      0.0675041000
_diffrn_orient_matrix_UB_12      0.0276469000
_diffrn_orient_matrix_UB_13      0.0107748000
_diffrn_orient_matrix_UB_21      0.0206873000
_diffrn_orient_matrix_UB_22      -0.0209527000
_diffrn_orient_matrix_UB_23      0.0473025000
_diffrn_orient_matrix_UB_31      0.0274305000
_diffrn_orient_matrix_UB_32      -0.0419672000
_diffrn_orient_matrix_UB_33      -0.0253856000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00   60.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412  179.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   86.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412   77.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00   46.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412  -77.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   84.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412   77.0000  -60.0000 96

#__ type_ start__ end____ width___ exp.time_
  5 omega   44.00   71.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412  179.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -44.00   49.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -      -18.6443   77.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
  7 omega  -12.00   88.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412   77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
  8 omega   34.00   94.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412  179.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega   -3.00   88.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412   53.0000  -70.0000 91

#__ type_ start__ end____ width___ exp.time_
 10 omega   34.00   94.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412  179.0000 -180.0000 60

#__ type_ start__ end____ width___ exp.time_
 11 omega  -52.00   48.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412  -77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 12 omega  -52.00   48.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -       17.9412  -77.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 13 omega  -49.00   12.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -      -18.6443   77.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
 14 omega  -49.00   51.00   1.0000   16.9300
omega____ theta____ kappa____ phi______ frames
    -      -18.6443   77.0000  -90.0000 100

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            36618
_reflns_number_total             8018
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_unetI/netI     0.1060
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 8018 
# Theoretical number of reflections is about 17718 


_diffrn_reflns_theta_min         4.151
_diffrn_reflns_theta_max         29.144
_diffrn_measured_fraction_theta_max 0.907

_diffrn_reflns_theta_full        25.064
_diffrn_measured_fraction_theta_full 0.983


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -13
_reflns_limit_h_max              12
_reflns_limit_k_min              -17
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.78
_oxford_diffrn_Wilson_scale      0.07

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.35
_refine_diff_density_max         0.39


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         6078
_refine_ls_number_restraints     20
_refine_ls_number_parameters     434
_oxford_refine_ls_R_factor_ref   0.0678
_refine_ls_wR_factor_ref         0.0662
_refine_ls_goodness_of_fit_ref   1.0757
_refine_ls_shift/su_max          0.0013347
_refine_ls_shift/su_mean         0.0000717


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        8018
_refine_ls_R_factor_all          0.0928
_refine_ls_wR_factor_all         0.0752

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6078
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_gt          0.0662

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 14.2 6.84 11.9 3.65 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 1.03330(14) 0.83587(10) 0.99002(10) 0.0402 1.0000 Uani . . . . . .
C2 C 0.98772(17) 0.85486(12) 1.07330(13) 0.0301 1.0000 Uani . . . . . .
C3 C 0.89717(16) 0.78302(11) 1.10387(12) 0.0258 1.0000 Uani . . . . . .
C4 C 0.86171(16) 0.68459(12) 1.04543(11) 0.0265 1.0000 Uani . . . . . .
N5 N 0.90721(14) 0.65810(10) 0.96308(10) 0.0292 1.0000 Uani . . . . . .
C6 C 0.87862(17) 0.55992(12) 0.90466(12) 0.0282 1.0000 Uani . . . . . .
C7 C 0.95890(19) 0.53436(14) 0.83392(14) 0.0370 1.0000 Uani . . . . . .
C8 C 0.9343(2) 0.43938(15) 0.77396(15) 0.0414 1.0000 Uani . . . . . .
C9 C 0.83026(19) 0.36852(13) 0.78261(14) 0.0370 1.0000 Uani . . . . . .
C10 C 0.7518(2) 0.39478(15) 0.85443(15) 0.0452 1.0000 Uani . . . . . .
C11 C 0.7745(2) 0.48885(15) 0.91467(14) 0.0413 1.0000 Uani . . . . . .
H111 H 0.7193 0.5044 0.9600 0.0505 1.0000 Uiso R . . . . .
H101 H 0.6809 0.3459 0.8612 0.0556 1.0000 Uiso R . . . . .
C12 C 0.7964(2) 0.26636(15) 0.71543(17) 0.0506 1.0000 Uani . . . . . .
C13 C 0.6656(2) 0.26421(14) 0.62740(16) 0.0494 1.0000 Uani D . . . . .
H331 H 0.5240 1.2313 1.3395 0.0468 1.0000 Uiso R . . . . .
H121 H 0.7800 0.2142 0.7567 0.0632 1.0000 Uiso R . . . . .
H122 H 0.8766 0.2505 0.6871 0.0622 1.0000 Uiso R . . . . .
H81 H 0.9911 0.4249 0.7271 0.0506 1.0000 Uiso R . . . . .
H71 H 1.0317 0.5825 0.8274 0.0455 1.0000 Uiso R . . . . .
H51 H 0.9672 0.7109 0.9501 0.0500 1.0000 Uiso R . . . . .
H41 H 0.8042 0.6371 1.0676 0.0344 1.0000 Uiso R . . . . .
C16 C 0.85181(16) 0.80744(11) 1.19871(12) 0.0259 1.0000 Uani . . . . . .
C17 C 0.90307(17) 0.90177(12) 1.26159(12) 0.0294 1.0000 Uani . . . . . .
C18 C 0.99271(18) 0.97223(12) 1.22667(14) 0.0354 1.0000 Uani . . . . . .
C19 C 1.03120(19) 0.95131(13) 1.13698(15) 0.0374 1.0000 Uani . . . . . .
H191 H 1.0876 0.9987 1.1157 0.0473 1.0000 Uiso R . . . . .
H181 H 1.0277 1.0349 1.2681 0.0430 1.0000 Uiso R . . . . .
C20 C 0.86775(19) 0.92363(13) 1.35732(13) 0.0364 1.0000 Uani . . . . . .
C21 C 0.7846(2) 0.85536(15) 1.39115(14) 0.0415 1.0000 Uani . . . . . .
C22 C 0.7301(2) 0.76346(14) 1.32811(14) 0.0396 1.0000 Uani . . . . . .
C23 C 0.76172(18) 0.74045(12) 1.23402(13) 0.0318 1.0000 Uani . . . . . .
H231 H 0.7219 0.6797 1.1921 0.0395 1.0000 Uiso R . . . . .
H221 H 0.6733 0.7170 1.3517 0.0480 1.0000 Uiso R . . . . .
H211 H 0.7639 0.8692 1.4551 0.0489 1.0000 Uiso R . . . . .
H201 H 0.9031 0.9859 1.3970 0.0452 1.0000 Uiso R . . . . .
O24 O 0.49167(14) 0.66623(9) 1.00812(10) 0.0414 1.0000 Uani . . . . . .
C25 C 0.40941(18) 0.64916(12) 0.91781(13) 0.0324 1.0000 Uani . . . . . .
C26 C 0.32042(16) 0.72561(11) 0.87167(13) 0.0287 1.0000 Uani . . . . . .
C27 C 0.32065(16) 0.82170(12) 0.92934(12) 0.0281 1.0000 Uani . . . . . .
N28 N 0.40183(14) 0.84808(10) 1.02248(10) 0.0284 1.0000 Uani . . . . . .
C29 C 0.40922(16) 0.94385(11) 1.08345(12) 0.0264 1.0000 Uani . . . . . .
C30 C 0.33337(17) 1.02613(12) 1.04863(12) 0.0304 1.0000 Uani . . . . . .
C31 C 0.34529(17) 1.11729(12) 1.11362(13) 0.0315 1.0000 Uani . . . . . .
C32 C 0.43176(17) 1.12988(12) 1.21319(12) 0.0293 1.0000 Uani . . . . . .
C33 C 0.43981(19) 1.22905(14) 1.28413(14) 0.0366 1.0000 Uani . . . . . .
C34 C 0.3103(2) 1.24118(16) 1.32862(17) 0.0487 1.0000 Uani . . . . . .
C35 C 0.3277(3) 1.33253(18) 1.41332(18) 0.0551 1.0000 Uani . . . . . .
C36 C 0.3631(4) 1.43333(19) 1.3803(2) 0.0739 1.0000 Uani . . . . . .
C46 C 0.1498(2) 0.77610(14) 0.71489(15) 0.0434 1.0000 Uani . . . . . .
H461 H 0.1459 0.8416 0.7510 0.0541 1.0000 Uiso R . . . . .
H332 H 0.4476 1.2885 1.2479 0.0464 1.0000 Uiso R . . . . .
C37 C 0.5099(2) 1.04817(15) 1.24535(14) 0.0413 1.0000 Uani . . . . . .
C38 C 0.4992(2) 0.95613(14) 1.18164(14) 0.0391 1.0000 Uani . . . . . .
H381 H 0.5538 0.9017 1.2059 0.0491 1.0000 Uiso R . . . . .
H371 H 0.5694 1.0534 1.3119 0.0508 1.0000 Uiso R . . . . .
H311 H 0.2948 1.1710 1.0884 0.0374 1.0000 Uiso R . . . . .
H301 H 0.2731 1.0201 0.9835 0.0387 1.0000 Uiso R . . . . .
H281 H 0.4582 0.8014 1.0464 0.0500 1.0000 Uiso R . . . . .
H271 H 0.2593 0.8699 0.8999 0.0350 1.0000 Uiso R . . . . .
C39 C 0.23543(17) 0.70465(12) 0.76612(13) 0.0305 1.0000 Uani . . . . . .
C40 C 0.23949(19) 0.60758(12) 0.70867(14) 0.0347 1.0000 Uani . . . . . .
C41 C 0.3242(2) 0.53242(13) 0.75871(15) 0.0402 1.0000 Uani . . . . . .
C42 C 0.4027(2) 0.55051(13) 0.85675(15) 0.0402 1.0000 Uani . . . . . .
H421 H 0.4538 0.4986 0.8865 0.0491 1.0000 Uiso R . . . . .
H411 H 0.3268 0.4675 0.7218 0.0502 1.0000 Uiso R . . . . .
C43 C 0.1604(2) 0.58718(15) 0.60543(15) 0.0451 1.0000 Uani . . . . . .
C44 C 0.0785(2) 0.65855(17) 0.55829(16) 0.0508 1.0000 Uani . . . . . .
C45 C 0.0732(2) 0.75348(17) 0.61369(17) 0.0519 1.0000 Uani . . . . . .
C141 C 0.6635(18) 0.1723(5) 0.5462(6) 0.0730 0.210(6) Uani D U P 1 2 .
C151 C 0.657(2) 0.0717(4) 0.5866(12) 0.0910 0.210(6) Uani D U P 1 2 .
H451 H 0.0158 0.8020 0.5819 0.0626 1.0000 Uiso R . . . . .
H441 H 0.0262 0.6436 0.4894 0.0617 1.0000 Uiso R . . . . .
H431 H 0.1664 0.5238 0.5707 0.0550 1.0000 Uiso R . . . . .
C14 C 0.6007(2) 0.15686(17) 0.5791(2) 0.0427 0.790(6) Uani D U P 1 1 .
C15 C 0.7036(3) 0.0908(2) 0.5409(3) 0.0638 0.790(6) Uani D U P 1 1 .
H141 H 0.5634 0.1254 0.6284 0.0770 0.790(6) Uiso R . P 1 1 .
H142 H 0.5253 0.1638 0.5208 0.0770 0.790(6) Uiso R . P 1 1 .
H1411 H 0.7570 0.1747 0.5351 0.0600 0.210(6) Uiso R . P 1 2 .
H1412 H 0.5953 0.1691 0.4819 0.0600 0.210(6) Uiso R . P 1 2 .
H1511 H 0.6658 0.0075 0.5491 0.0600 0.210(6) Uiso R . P 1 2 .
H1512 H 0.7258 0.0798 0.6511 0.0600 0.210(6) Uiso R . P 1 2 .
H1513 H 0.5641 0.0742 0.5979 0.0600 0.210(6) Uiso R . P 1 2 .
H151 H 0.6556 0.0260 0.5115 0.1133 0.790(6) Uiso R . P 1 1 .
H152 H 0.7793 0.0819 0.5983 0.1133 0.790(6) Uiso R . P 1 1 .
H153 H 0.7412 0.1203 0.4907 0.1133 0.790(6) Uiso R . P 1 1 .
H131 H 0.5946 0.2993 0.6528 0.0610 0.790(6) Uiso R . P . . .
H132 H 0.6910 0.2993 0.5756 0.0610 0.790(6) Uiso R . P . . .
H133 H 0.6616 0.3274 0.5990 0.0610 0.210(6) Uiso R . P . . .
H134 H 0.5809 0.2515 0.6496 0.0610 0.210(6) Uiso R . P . . .
H341 H 0.2925 1.1800 1.3564 0.0606 1.0000 Uiso R . . . . .
H342 H 0.2307 1.2511 1.2744 0.0606 1.0000 Uiso R . . . . .
H351 H 0.4025 1.3204 1.4699 0.0671 1.0000 Uiso R . . . . .
H352 H 0.2410 1.3369 1.4347 0.0671 1.0000 Uiso R . . . . .
H361 H 0.3656 1.4876 1.4377 0.0903 1.0000 Uiso R . . . . .
H362 H 0.4613 1.4278 1.3664 0.0903 1.0000 Uiso R . . . . .
H363 H 0.2933 1.4449 1.3172 0.0903 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.568(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.300(2) yes
C2 . C3 . 1.420(2) yes
C2 . C19 . 1.435(2) yes
C3 . C4 . 1.420(2) yes
C3 . C16 . 1.451(2) yes
C4 . N5 . 1.302(2) yes
C4 . H41 . 0.938 no
N5 . C6 . 1.414(2) yes
N5 . H51 . 0.944 no
C6 . C7 . 1.385(2) yes
C6 . C11 . 1.386(2) yes
C7 . C8 . 1.387(2) yes
C7 . H71 . 0.954 no
C8 . C9 . 1.377(3) yes
C8 . H81 . 0.937 no
C9 . C10 . 1.385(3) yes
C9 . C12 . 1.509(2) yes
C10 . C11 . 1.379(3) yes
C10 . H101 . 0.948 no
C11 . H111 . 0.912 no
C12 . C13 . 1.509(3) yes
C12 . H121 . 0.959 no
C12 . H122 . 0.961 no
C13 . C14 . 1.529(2) yes
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 no
C13 . H134 . 0.950 no
C13 . C141 . 1.530(3) yes
C13 . H131 . 0.950 no
C13 . H132 . 0.950 no
C13 . H133 . 0.950 no
C13 . H134 . 0.950 no
H331 . C33 . 0.961 no
C16 . C17 . 1.419(2) yes
C16 . C23 . 1.410(2) yes
C17 . C18 . 1.433(2) yes
C17 . C20 . 1.410(2) yes
C18 . C19 . 1.347(3) yes
C18 . H181 . 0.943 no
C19 . H191 . 0.925 no
C20 . C21 . 1.365(3) yes
C20 . H201 . 0.930 no
C21 . C22 . 1.401(3) yes
C21 . H211 . 0.928 no
C22 . C23 . 1.374(2) yes
C22 . H221 . 0.935 no
C23 . H231 . 0.936 no
O24 . C25 . 1.274(2) yes
C25 . C26 . 1.445(2) yes
C25 . C42 . 1.445(2) yes
C26 . C27 . 1.405(2) yes
C26 . C39 . 1.451(2) yes
C27 . N28 . 1.311(2) yes
C27 . H271 . 0.940 no
N28 . C29 . 1.4123(19) yes
N28 . H281 . 0.874 no
C29 . C30 . 1.392(2) yes
C29 . C38 . 1.386(2) yes
C30 . C31 . 1.385(2) yes
C30 . H301 . 0.922 no
C31 . C32 . 1.388(2) yes
C31 . H311 . 0.924 no
C32 . C33 . 1.514(2) yes
C32 . C37 . 1.387(2) yes
C33 . C34 . 1.516(3) yes
C33 . H332 . 0.975 no
C34 . C35 . 1.534(3) yes
C34 . H341 . 0.950 no
C34 . H342 . 0.950 no
C35 . C36 . 1.495(4) yes
C35 . H351 . 0.950 no
C35 . H352 . 0.950 no
C36 . H361 . 0.986 no
C36 . H362 . 1.013 no
C36 . H363 . 0.981 no
C46 . H461 . 0.947 no
C46 . C39 . 1.405(3) yes
C46 . C45 . 1.379(3) yes
C37 . C38 . 1.387(2) yes
C37 . H371 . 0.935 no
C38 . H381 . 0.946 no
C39 . C40 . 1.422(2) yes
C40 . C41 . 1.431(3) yes
C40 . C43 . 1.406(3) yes
C41 . C42 . 1.345(3) yes
C41 . H411 . 0.942 no
C42 . H421 . 0.929 no
C43 . C44 . 1.364(3) yes
C43 . H431 . 0.919 no
C44 . C45 . 1.389(3) yes
C44 . H441 . 0.938 no
C45 . H451 . 0.934 no
C141 . C151 . 1.488(5) yes
C141 . H1411 . 0.950 no
C141 . H1412 . 0.950 no
C151 . H1511 . 0.950 no
C151 . H1512 . 0.950 no
C151 . H1513 . 0.950 no
C14 . C15 . 1.489(3) yes
C14 . H141 . 0.950 no
C14 . H142 . 0.950 no
C15 . H151 . 0.950 no
C15 . H152 . 0.950 no
C15 . H153 . 0.950 no
H131 . H134 . 0.632 no
H132 . H133 . 0.583 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . C3 . 122.21(14) yes
O1 . C2 . C19 . 118.93(15) yes
C3 . C2 . C19 . 118.86(15) yes
C2 . C3 . C4 . 119.31(14) yes
C2 . C3 . C16 . 119.87(14) yes
C4 . C3 . C16 . 120.62(14) yes
C3 . C4 . N5 . 122.28(14) yes
C3 . C4 . H41 . 118.5 no
N5 . C4 . H41 . 119.2 no
C4 . N5 . C6 . 124.17(14) yes
C4 . N5 . H51 . 111.5 no
C6 . N5 . H51 . 124.1 no
N5 . C6 . C7 . 117.92(15) yes
N5 . C6 . C11 . 123.26(15) yes
C7 . C6 . C11 . 118.82(15) yes
C6 . C7 . C8 . 120.25(17) yes
C6 . C7 . H71 . 119.2 no
C8 . C7 . H71 . 120.5 no
C7 . C8 . C9 . 121.41(17) yes
C7 . C8 . H81 . 117.7 no
C9 . C8 . H81 . 120.9 no
C8 . C9 . C10 . 117.67(16) yes
C8 . C9 . C12 . 122.77(18) yes
C10 . C9 . C12 . 119.53(18) yes
C9 . C10 . C11 . 121.78(18) yes
C9 . C10 . H101 . 117.9 no
C11 . C10 . H101 . 120.3 no
C6 . C11 . C10 . 120.06(17) yes
C6 . C11 . H111 . 120.4 no
C10 . C11 . H111 . 119.5 no
C9 . C12 . C13 . 113.51(15) yes
C9 . C12 . H121 . 109.2 no
C13 . C12 . H121 . 107.6 no
C9 . C12 . H122 . 108.8 no
C13 . C12 . H122 . 108.4 no
H121 . C12 . H122 . 109.3 no
C12 . C13 . C14 . 114.88(18) yes
C12 . C13 . H131 . 108.1 no
C14 . C13 . H131 . 107.5 no
C12 . C13 . H132 . 108.0 no
C14 . C13 . H132 . 108.9 no
H131 . C13 . H132 . 109.5 no
C12 . C13 . H133 . 110.5 no
C14 . C13 . H133 . 130.5 no
H131 . C13 . H133 . 75.2 no
H132 . C13 . H133 . 35.8 no
C12 . C13 . H134 . 111.1 no
C14 . C13 . H134 . 71.6 no
H131 . C13 . H134 . 38.8 no
H132 . C13 . H134 . 136.1 no
H133 . C13 . H134 . 109.5 no
C12 . C13 . C141 . 110.1(6) yes
C12 . C13 . H131 . 108.1 no
C141 . C13 . H131 . 134.7 no
C12 . C13 . H132 . 108.0 no
C141 . C13 . H132 . 80.8 no
H131 . C13 . H132 . 109.5 no
C12 . C13 . H133 . 110.5 no
C141 . C13 . H133 . 112.1 no
H131 . C13 . H133 . 75.2 no
H132 . C13 . H133 . 35.8 no
C12 . C13 . H134 . 111.1 no
C141 . C13 . H134 . 103.4 no
H131 . C13 . H134 . 38.8 no
H132 . C13 . H134 . 136.1 no
H133 . C13 . H134 . 109.5 no
C3 . C16 . C17 . 119.18(14) yes
C3 . C16 . C23 . 123.24(14) yes
C17 . C16 . C23 . 117.54(14) yes
C16 . C17 . C18 . 118.75(15) yes
C16 . C17 . C20 . 119.89(15) yes
C18 . C17 . C20 . 121.35(15) yes
C17 . C18 . C19 . 122.20(15) yes
C17 . C18 . H181 . 119.3 no
C19 . C18 . H181 . 118.5 no
C2 . C19 . C18 . 121.02(16) yes
C2 . C19 . H191 . 118.6 no
C18 . C19 . H191 . 120.4 no
C17 . C20 . C21 . 121.12(16) yes
C17 . C20 . H201 . 118.0 no
C21 . C20 . H201 . 120.9 no
C20 . C21 . C22 . 119.30(16) yes
C20 . C21 . H211 . 120.9 no
C22 . C21 . H211 . 119.8 no
C21 . C22 . C23 . 120.86(17) yes
C21 . C22 . H221 . 119.0 no
C23 . C22 . H221 . 120.2 no
C16 . C23 . C22 . 121.21(15) yes
C16 . C23 . H231 . 119.2 no
C22 . C23 . H231 . 119.5 no
O24 . C25 . C26 . 122.57(15) yes
O24 . C25 . C42 . 120.24(16) yes
C26 . C25 . C42 . 117.19(16) yes
C25 . C26 . C27 . 119.10(15) yes
C25 . C26 . C39 . 120.45(14) yes
C27 . C26 . C39 . 120.42(14) yes
C26 . C27 . N28 . 123.59(15) yes
C26 . C27 . H271 . 118.6 no
N28 . C27 . H271 . 117.8 no
C27 . N28 . C29 . 126.33(14) yes
C27 . N28 . H281 . 114.8 no
C29 . N28 . H281 . 118.8 no
N28 . C29 . C30 . 123.16(14) yes
N28 . C29 . C38 . 117.75(14) yes
C30 . C29 . C38 . 119.08(14) yes
C29 . C30 . C31 . 119.64(15) yes
C29 . C30 . H301 . 120.8 no
C31 . C30 . H301 . 119.5 no
C30 . C31 . C32 . 121.98(15) yes
C30 . C31 . H311 . 118.0 no
C32 . C31 . H311 . 120.0 no
C31 . C32 . C33 . 121.15(15) yes
C31 . C32 . C37 . 117.54(14) yes
C33 . C32 . C37 . 121.31(15) yes
C32 . C33 . H331 . 108.4 no
C32 . C33 . C34 . 113.42(15) yes
H331 . C33 . C34 . 109.3 no
C32 . C33 . H332 . 111.2 no
H331 . C33 . H332 . 107.8 no
C34 . C33 . H332 . 106.5 no
C33 . C34 . C35 . 113.65(16) yes
C33 . C34 . H341 . 108.3 no
C35 . C34 . H341 . 108.9 no
C33 . C34 . H342 . 108.5 no
C35 . C34 . H342 . 108.0 no
H341 . C34 . H342 . 109.5 no
C34 . C35 . C36 . 114.02(19) yes
C34 . C35 . H351 . 108.2 no
C36 . C35 . H351 . 108.2 no
C34 . C35 . H352 . 108.5 no
C36 . C35 . H352 . 108.3 no
H351 . C35 . H352 . 109.5 no
C35 . C36 . H361 . 108.2 no
C35 . C36 . H362 . 105.4 no
H361 . C36 . H362 . 110.6 no
C35 . C36 . H363 . 110.4 no
H361 . C36 . H363 . 111.8 no
H362 . C36 . H363 . 110.2 no
H461 . C46 . C39 . 118.7 no
H461 . C46 . C45 . 119.5 no
C39 . C46 . C45 . 121.75(17) yes
C32 . C37 . C38 . 121.38(16) yes
C32 . C37 . H371 . 120.3 no
C38 . C37 . H371 . 118.3 no
C37 . C38 . C29 . 120.32(16) yes
C37 . C38 . H381 . 119.4 no
C29 . C38 . H381 . 120.3 no
C26 . C39 . C46 . 123.80(14) yes
C26 . C39 . C40 . 119.32(15) yes
C46 . C39 . C40 . 116.87(16) yes
C39 . C40 . C41 . 118.44(16) yes
C39 . C40 . C43 . 119.91(17) yes
C41 . C40 . C43 . 121.65(16) yes
C40 . C41 . C42 . 122.87(15) yes
C40 . C41 . H411 . 119.3 no
C42 . C41 . H411 . 117.8 no
C25 . C42 . C41 . 121.59(17) yes
C25 . C42 . H421 . 118.8 no
C41 . C42 . H421 . 119.6 no
C40 . C43 . C44 . 121.52(17) yes
C40 . C43 . H431 . 117.3 no
C44 . C43 . H431 . 121.1 no
C43 . C44 . C45 . 119.11(19) yes
C43 . C44 . H441 . 120.4 no
C45 . C44 . H441 . 120.5 no
C44 . C45 . C46 . 120.8(2) yes
C44 . C45 . H451 . 119.2 no
C46 . C45 . H451 . 120.0 no
C13 . C141 . C151 . 113.31(5) yes
C13 . C141 . H1411 . 104.6 no
C151 . C141 . H1411 . 101.0 no
C13 . C141 . H1412 . 117.9 no
C151 . C141 . H1412 . 109.0 no
H1411 . C141 . H1412 . 109.5 no
C141 . C151 . H1511 . 124.4 no
C141 . C151 . H1512 . 105.4 no
H1511 . C151 . H1512 . 109.5 no
C141 . C151 . H1513 . 97.5 no
H1511 . C151 . H1513 . 109.5 no
H1512 . C151 . H1513 . 109.5 no
C13 . C14 . C15 . 113.31(5) yes
C13 . C14 . H141 . 108.7 no
C15 . C14 . H141 . 110.5 no
C13 . C14 . H142 . 108.2 no
C15 . C14 . H142 . 106.6 no
H141 . C14 . H142 . 109.5 no
C14 . C15 . H151 . 108.4 no
C14 . C15 . H152 . 108.0 no
H151 . C15 . H152 . 109.5 no
C14 . C15 . H153 . 111.9 no
H151 . C15 . H153 . 109.5 no
H152 . C15 . H153 . 109.5 no
C13 . H131 . H134 . 70.6 no
C13 . H132 . H133 . 72.1 no
H132 . H133 . C13 . 72.1 no
H131 . H134 . C13 . 70.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N5 . H51 . O1 . 143.57(6) 0.944 1.718 2.540(3) yes
N28 . H281 . O24 . 138.59(6) 0.874 1.856 2.577(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/04/14 at 16:00:33
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
EQUIV C(14,OCC) C(141,OCC) C(15,OCC) C(151,OCC) 
CONT H(131,OCC) H(132,OCC) H(133,OCC) H(134,OCC) 
CONT H(141,OCC) H(142,OCC) H(1411,OCC) H(1412,OCC) 
CONT H(151,OCC) H(152,OCC) H(153,OCC) 
CONT H(1511,OCC) H(1512,OCC) H(1513,OCC) 
WEIGHT -1 C(141,OCC) C(151,OCC) 
CONT  H(133,OCC) H(134,OCC) 
CONT  H(1411,OCC) H(1412,OCC) 
CONT H(1511,OCC) H(1512,OCC) H(1513,OCC) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE N   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE N   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) 
RIDE C   (  35,X'S) H   ( 352,X'S) H   ( 351,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 363,X'S) H   ( 362,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C(13,X'S) H(131,X'S) H(132,X'S) H(133,X'S) H(134,X'S) 
RIDE C(14,X'S) H(141,X'S) H(142,X'S) 
RIDE C(141,X'S) H(1411,X'S) H(1412,X'S) 
RIDE C(15,X'S) H(151,X'S) H(152,X'S)  H(153,X'S) 
RIDE C(151,X'S) H(1511,X'S) H(1512,X'S) H(1513,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/04/14 at 16:00:33
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
DIST 1.52,0.005 = C(13) TO C(14), C(13) TO C(141) 
SAME 0.005 , 0.05 
CONT C(13)  C(14)  C(15) AND 
CONT  C(13)  C(141)  C(151) 
A-U(IJ)'S 0.0,0.05 = C(14) TO C(141), C(15) TO C(151) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_13
_database_code_depnum_ccdc_archive 'CCDC 1058504'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_exptl_special_details           
;
 The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
_cell_length_a                   5.04160(18)
_cell_length_b                   13.6467(5)
_cell_length_c                   31.0182(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.550(3)
_cell_angle_gamma                90
_cell_volume                     2127.37(13)
_cell_measurement_reflns_used    4995
_cell_measurement_theta_min      4.5780
_cell_measurement_theta_max      28.9480
_cell_oxdiff_length_a            5.04159(15)
_cell_oxdiff_length_b            13.6457(7)
_cell_oxdiff_length_c            31.0207(12)
_cell_oxdiff_angle_alpha         89.994(4)
_cell_oxdiff_angle_beta          94.550(3)
_cell_oxdiff_angle_gamma         90.001(3)
_cell_oxdiff_volume              2127.37(16)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C25 H27 N O6'
_chemical_formula_moiety         'C25 H27 N O6'
_chemical_compound_source        ?
_chemical_formula_weight         437.48


_cell_measurement_temperature    175

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.300
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_max          0.550
_exptl_absorpt_correction_T_min  0.99101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.098
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.73
_montpellier_reflns_completeness_maxres 90.61
_montpellier_reflns_redundancy_maxres 4.58

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.63 6.5 98.83 0.015 96.0 96.04
1 1.63 1.30 6.3 34.95 0.033 100.0 97.98
2 1.30 1.14 5.9 25.93 0.036 100.0 98.64
3 1.14 1.03 5.2 19.68 0.048 100.0 98.98
4 1.03 0.96 4.8 12.56 0.072 100.0 99.18
5 0.96 0.90 4.5 9.44 0.097 100.0 99.32
6 0.90 0.85 4.1 7.64 0.120 100.0 99.41
7 0.85 0.82 3.8 5.37 0.170 100.0 99.49
8 0.82 0.79 3.1 4.96 0.172 98.2 99.34
9 0.79 0.73 1.7 3.42 0.172 50.8 90.61
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      -0.0194145000
_diffrn_orient_matrix_UB_12      -0.0162489000
_diffrn_orient_matrix_UB_13      -0.0217403000
_diffrn_orient_matrix_UB_21      0.0062943000
_diffrn_orient_matrix_UB_22      0.0491713000
_diffrn_orient_matrix_UB_23      -0.0072649000
_diffrn_orient_matrix_UB_31      0.1396503000
_diffrn_orient_matrix_UB_32      -0.0044750000
_diffrn_orient_matrix_UB_33      -0.0008565000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9412    0.0000  150.0000 116

#__ type_ start__ end____ width___ exp.time_
  2 omega   30.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9412 -149.0000 -131.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7224   38.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega  -77.00  -49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7224  130.0000   53.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega   -8.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9412   38.0000    0.0000 98

#__ type_ start__ end____ width___ exp.time_
  6 omega   -8.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9412   38.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
  7 omega  -12.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9412   77.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega  -86.00  -29.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7224  141.0000 -132.0000 57

;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            23748
_reflns_number_total             5125
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_unetI/netI     0.0450
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 5125
# Theoretical number of reflections is about 11321


_diffrn_reflns_theta_min         4.321
_diffrn_reflns_theta_max         29.007
_diffrn_measured_fraction_theta_max 0.906

_diffrn_reflns_theta_full        25.236
_diffrn_measured_fraction_theta_full 0.978


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       39
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              41

_oxford_diffrn_Wilson_B_factor   2.49
_oxford_diffrn_Wilson_scale      0.04

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.32
_refine_diff_density_max         0.68


# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold


# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     0
_refine_ls_number_parameters     289
_oxford_refine_ls_R_factor_ref   0.0520
_refine_ls_wR_factor_ref         0.0549
_refine_ls_goodness_of_fit_ref   1.1293
_refine_ls_shift/su_max          0.0006944
_refine_ls_shift/su_mean         0.0000507


# The values computed with all filters except I/sigma
_oxford_reflns_number_all        5125
_refine_ls_R_factor_all          0.0691
_refine_ls_wR_factor_all         0.0620

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4041
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_gt          0.0549

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are:
 13.5 5.73 11.2 3.79 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.2637(2) 0.80227(8) 0.52711(3) 0.0252 1.0000 Uani . . . . . .
C2 C 0.0928(3) 0.88377(10) 0.53298(5) 0.0239 1.0000 Uani . . . . . .
C3 C -0.0217(3) 0.86878(11) 0.57588(5) 0.0265 1.0000 Uani . . . . . .
O4 O 0.1743(2) 0.89172(8) 0.61006(4) 0.0307 1.0000 Uani . . . . . .
C5 C 0.2078(3) 0.81876(12) 0.64316(5) 0.0314 1.0000 Uani . . . . . .
C6 C 0.3863(3) 0.73633(12) 0.63038(5) 0.0317 1.0000 Uani . . . . . .
O7 O 0.4344(2) 0.67635(10) 0.66788(4) 0.0378 1.0000 Uani . . . . . .
C8 C 0.5295(4) 0.57937(13) 0.65839(6) 0.0395 1.0000 Uani . . . . . .
C9 C 0.8085(4) 0.57557(13) 0.64493(5) 0.0366 1.0000 Uani . . . . . .
O10 O 0.8299(3) 0.60847(8) 0.60165(4) 0.0357 1.0000 Uani . . . . . .
C11 C 0.7621(4) 0.53675(12) 0.57001(6) 0.0368 1.0000 Uani . . . . . .
C12 C 0.7806(4) 0.58397(12) 0.52658(5) 0.0344 1.0000 Uani . . . . . .
O13 O 0.5677(2) 0.65288(8) 0.52069(4) 0.0328 1.0000 Uani . . . . . .
C14 C 0.5849(3) 0.72260(10) 0.48953(5) 0.0246 1.0000 Uani . . . . . .
C15 C 0.4178(3) 0.80438(11) 0.49286(4) 0.0224 1.0000 Uani . . . . . .
C16 C 0.4232(3) 0.87881(11) 0.46261(5) 0.0251 1.0000 Uani . . . . . .
C17 C 0.5939(3) 0.87459(11) 0.42927(5) 0.0263 1.0000 Uani . . . . . .
C18 C 0.7595(3) 0.79421(11) 0.42624(4) 0.0252 1.0000 Uani . . . . . .
C19 C 0.7517(3) 0.71799(11) 0.45625(5) 0.0275 1.0000 Uani . . . . . .
H191 H 0.8637 0.6635 0.4538 0.0326 1.0000 Uiso R . . . . .
N20 N 0.9411(3) 0.78184(10) 0.39414(4) 0.0302 1.0000 Uani . . . . . .
C21 C 1.0107(3) 0.85054(12) 0.36853(4) 0.0274 1.0000 Uani . . . . . .
C22 C 1.2034(3) 0.83225(12) 0.33769(4) 0.0274 1.0000 Uani . . . . . .
C23 C 1.2855(3) 0.90912(12) 0.30940(4) 0.0267 1.0000 Uani . . . . . .
C24 C 1.4796(3) 0.88769(13) 0.27989(5) 0.0306 1.0000 Uani . . . . . .
C25 C 1.5592(3) 0.96228(15) 0.25196(5) 0.0375 1.0000 Uani . . . . . .
C26 C 1.4537(4) 1.05395(15) 0.25249(5) 0.0400 1.0000 Uani . . . . . .
C27 C 1.2626(4) 1.07561(15) 0.28158(6) 0.0397 1.0000 Uani . . . . . .
C28 C 1.1818(3) 1.00507(13) 0.30945(5) 0.0336 1.0000 Uani . . . . . .
H281 H 1.0518 1.0211 0.3283 0.0399 1.0000 Uiso R . . . . .
H271 H 1.1866 1.1385 0.2820 0.0479 1.0000 Uiso R . . . . .
H261 H 1.5050 1.1026 0.2334 0.0484 1.0000 Uiso R . . . . .
H251 H 1.6859 0.9468 0.2329 0.0445 1.0000 Uiso R . . . . .
C29 C 1.5890(3) 0.79179(14) 0.27896(5) 0.0375 1.0000 Uani . . . . . .
C30 C 1.5146(4) 0.72022(14) 0.30564(6) 0.0403 1.0000 Uani . . . . . .
C31 C 1.3203(4) 0.73873(13) 0.33567(5) 0.0345 1.0000 Uani . . . . . .
O32 O 1.2574(3) 0.66636(9) 0.36104(5) 0.0482 1.0000 Uani . . . . . .
H301 H 1.5914 0.6571 0.3051 0.0482 1.0000 Uiso R . . . . .
H291 H 1.7163 0.7786 0.2594 0.0450 1.0000 Uiso R . . . . .
H211 H 0.9328 0.9146 0.3704 0.0331 1.0000 Uiso R . . . . .
H171 H 0.5934 0.9259 0.4092 0.0312 1.0000 Uiso R . . . . .
H161 H 0.3093 0.9333 0.4642 0.0299 1.0000 Uiso R . . . . .
H122 H 0.9540 0.6182 0.5257 0.0414 1.0000 Uiso R . . . . .
H121 H 0.7687 0.5354 0.5041 0.0416 1.0000 Uiso R . . . . .
H112 H 0.8849 0.4818 0.5731 0.0436 1.0000 Uiso R . . . . .
H111 H 0.5820 0.5120 0.5720 0.0430 1.0000 Uiso R . . . . .
H92 H 0.9220 0.6208 0.6652 0.0445 1.0000 Uiso R . . . . .
H91 H 0.8752 0.5072 0.6485 0.0434 1.0000 Uiso R . . . . .
H82 H 0.5332 0.5417 0.6859 0.0485 1.0000 Uiso R . . . . .
H81 H 0.4025 0.5470 0.6360 0.0476 1.0000 Uiso R . . . . .
H62 H 0.5502 0.7636 0.6214 0.0381 1.0000 Uiso R . . . . .
H61 H 0.2993 0.6982 0.6066 0.0377 1.0000 Uiso R . . . . .
H52 H 0.2882 0.8515 0.6686 0.0384 1.0000 Uiso R . . . . .
H51 H 0.0377 0.7925 0.6501 0.0371 1.0000 Uiso R . . . . .
H32 H -0.1760 0.9125 0.5774 0.0325 1.0000 Uiso R . . . . .
H31 H -0.0831 0.8013 0.5780 0.0315 1.0000 Uiso R . . . . .
H22 H 0.1912 0.9444 0.5329 0.0279 1.0000 Uiso R . . . . .
H21 H -0.0487 0.8867 0.5091 0.0289 1.0000 Uiso R . . . . .
H321 H 1.1185 0.6906 0.3790 0.0500 0.5000 Uiso R . . 1 2 .
H201 H 1.0134 0.7246 0.3908 0.0500 0.5000 Uiso R . . 2 1 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.707(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.4273(17) yes
O1 . C15 . 1.3652(16) yes
C2 . C3 . 1.506(2) yes
C2 . H22 . 0.964 no
C2 . H21 . 0.987 no
C3 . O4 . 1.4257(19) yes
C3 . H32 . 0.985 no
C3 . H31 . 0.976 no
O4 . C5 . 1.4305(18) yes
C5 . C6 . 1.513(2) yes
C5 . H52 . 0.967 no
C5 . H51 . 0.969 no
C6 . O7 . 1.4272(18) yes
C6 . H62 . 0.967 no
C6 . H61 . 0.978 no
O7 . C8 . 1.446(2) yes
C8 . C9 . 1.500(2) yes
C8 . H82 . 0.995 no
C8 . H81 . 1.007 no
C9 . O10 . 1.4277(19) yes
C9 . H92 . 1.022 no
C9 . H91 . 0.996 no
O10 . C11 . 1.409(2) yes
C11 . C12 . 1.503(2) yes
C11 . H112 . 0.972 no
C11 . H111 . 0.976 no
C12 . O13 . 1.4280(19) yes
C12 . H122 . 0.994 no
C12 . H121 . 0.960 no
O13 . C14 . 1.3640(17) yes
C14 . C15 . 1.407(2) yes
C14 . C19 . 1.3835(19) yes
C15 . C16 . 1.3845(19) yes
C16 . C17 . 1.398(2) yes
C16 . H161 . 0.943 no
C17 . C18 . 1.386(2) yes
C17 . H171 . 0.938 no
C18 . C19 . 1.399(2) yes
C18 . N20 . 1.4151(18) yes
C19 . H191 . 0.940 no
N20 . C21 . 1.2950(19) yes
N20 . H201 . 0.872 no
C21 . C22 . 1.438(2) yes
C21 . H211 . 0.962 no
C22 . C23 . 1.449(2) yes
C22 . C31 . 1.409(2) yes
C23 . C24 . 1.422(2) yes
C23 . C28 . 1.410(2) yes
C24 . C25 . 1.415(2) yes
C24 . C29 . 1.421(3) yes
C25 . C26 . 1.360(3) yes
C25 . H251 . 0.929 no
C26 . C27 . 1.403(3) yes
C26 . H261 . 0.939 no
C27 . C28 . 1.377(2) yes
C27 . H271 . 0.941 no
C28 . H281 . 0.938 no
C29 . C30 . 1.352(3) yes
C29 . H291 . 0.935 no
C30 . C31 . 1.427(2) yes
C30 . H301 . 0.945 no
C31 . O32 . 1.317(2) yes
O32 . H321 . 0.987 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C15 . 117.99(11) yes
O1 . C2 . C3 . 106.53(11) yes
O1 . C2 . H22 . 110.6 no
C3 . C2 . H22 . 110.6 no
O1 . C2 . H21 . 110.1 no
C3 . C2 . H21 . 111.3 no
H22 . C2 . H21 . 107.8 no
C2 . C3 . O4 . 109.61(12) yes
C2 . C3 . H32 . 108.6 no
O4 . C3 . H32 . 109.6 no
C2 . C3 . H31 . 109.5 no
O4 . C3 . H31 . 111.3 no
H32 . C3 . H31 . 108.2 no
C3 . O4 . C5 . 114.60(12) yes
O4 . C5 . C6 . 111.60(12) yes
O4 . C5 . H52 . 106.3 no
C6 . C5 . H52 . 109.7 no
O4 . C5 . H51 . 111.1 no
C6 . C5 . H51 . 109.8 no
H52 . C5 . H51 . 108.1 no
C5 . C6 . O7 . 106.19(12) yes
C5 . C6 . H62 . 109.2 no
O7 . C6 . H62 . 111.2 no
C5 . C6 . H61 . 110.7 no
O7 . C6 . H61 . 110.3 no
H62 . C6 . H61 . 109.2 no
C6 . O7 . C8 . 113.37(13) yes
O7 . C8 . C9 . 114.95(15) yes
O7 . C8 . H82 . 106.4 no
C9 . C8 . H82 . 105.5 no
O7 . C8 . H81 . 109.8 no
C9 . C8 . H81 . 110.7 no
H82 . C8 . H81 . 109.3 no
C8 . C9 . O10 . 113.15(14) yes
C8 . C9 . H92 . 107.5 no
O10 . C9 . H92 . 107.9 no
C8 . C9 . H91 . 108.5 no
O10 . C9 . H91 . 110.5 no
H92 . C9 . H91 . 109.2 no
C9 . O10 . C11 . 113.86(13) yes
O10 . C11 . C12 . 107.32(13) yes
O10 . C11 . H112 . 110.5 no
C12 . C11 . H112 . 109.5 no
O10 . C11 . H111 . 111.8 no
C12 . C11 . H111 . 109.3 no
H112 . C11 . H111 . 108.4 no
C11 . C12 . O13 . 107.33(12) yes
C11 . C12 . H122 . 110.1 no
O13 . C12 . H122 . 109.9 no
C11 . C12 . H121 . 110.5 no
O13 . C12 . H121 . 111.0 no
H122 . C12 . H121 . 108.1 no
C12 . O13 . C14 . 117.42(11) yes
O13 . C14 . C15 . 115.39(12) yes
O13 . C14 . C19 . 125.00(13) yes
C15 . C14 . C19 . 119.60(13) yes
C14 . C15 . O1 . 114.93(12) yes
C14 . C15 . C16 . 119.20(13) yes
O1 . C15 . C16 . 125.87(13) yes
C15 . C16 . C17 . 121.16(14) yes
C15 . C16 . H161 . 119.9 no
C17 . C16 . H161 . 119.0 no
C16 . C17 . C18 . 119.47(13) yes
C16 . C17 . H171 . 119.5 no
C18 . C17 . H171 . 121.1 no
C17 . C18 . C19 . 119.65(13) yes
C17 . C18 . N20 . 124.66(13) yes
C19 . C18 . N20 . 115.68(13) yes
C18 . C19 . C14 . 120.89(14) yes
C18 . C19 . H191 . 119.0 no
C14 . C19 . H191 . 120.1 no
C18 . N20 . C21 . 124.54(14) yes
C18 . N20 . H201 . 119.3 no
C21 . N20 . H201 . 116.2 no
N20 . C21 . C22 . 120.83(15) yes
N20 . C21 . H211 . 119.3 no
C22 . C21 . H211 . 119.9 no
C21 . C22 . C23 . 121.18(14) yes
C21 . C22 . C31 . 119.59(14) yes
C23 . C22 . C31 . 119.21(13) yes
C22 . C23 . C24 . 119.01(15) yes
C22 . C23 . C28 . 123.24(13) yes
C24 . C23 . C28 . 117.75(14) yes
C23 . C24 . C25 . 119.28(16) yes
C23 . C24 . C29 . 119.36(15) yes
C25 . C24 . C29 . 121.36(15) yes
C24 . C25 . C26 . 121.58(15) yes
C24 . C25 . H251 . 118.0 no
C26 . C25 . H251 . 120.4 no
C25 . C26 . C27 . 119.41(16) yes
C25 . C26 . H261 . 121.0 no
C27 . C26 . H261 . 119.6 no
C26 . C27 . C28 . 120.59(18) yes
C26 . C27 . H271 . 120.1 no
C28 . C27 . H271 . 119.3 no
C23 . C28 . C27 . 121.38(15) yes
C23 . C28 . H281 . 119.6 no
C27 . C28 . H281 . 119.0 no
C24 . C29 . C30 . 121.73(15) yes
C24 . C29 . H291 . 118.5 no
C30 . C29 . H291 . 119.7 no
C29 . C30 . C31 . 120.64(17) yes
C29 . C30 . H301 . 120.9 no
C31 . C30 . H301 . 118.5 no
C30 . C31 . C22 . 120.05(15) yes
C30 . C31 . O32 . 117.88(16) yes
C22 . C31 . O32 . 122.08(15) yes
C31 . O32 . H321 . 107.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C28 . H281 . O4 2_676 159.48(4) 0.938 2.592 3.486(2) yes
C9 . H91 . O32 2_766 143.04(6) 0.996 2.472 3.322(2) yes
O32 . H321 . N20 . 148.45(6) 0.987 1.624 2.518(2) yes
N20 . H201 . O32 . 140.56(6) 0.872 1.783 2.518(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/04/14 at 17:09:26
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  22,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  32,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  52,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  82,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  92,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 112,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE N   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE O   (  32,X'S) H   ( 321,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/04/14 at 17:09:26
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1058505'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_exptl_special_details           
;
 The crystal was
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#---------------------------------------------------------------
_cell_length_a                   46.312(3)
_cell_length_b                   46.312(3)
_cell_length_c                   5.6266(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10451.3(14)
_cell_measurement_reflns_used    1100
_cell_measurement_theta_min      4.1448
_cell_measurement_theta_max      28.8531
_cell_oxdiff_length_a            46.301(3)
_cell_oxdiff_length_b            46.293(4)
_cell_oxdiff_length_c            5.6263(5)
_cell_oxdiff_angle_alpha         90.001(7)
_cell_oxdiff_angle_beta          90.009(6)
_cell_oxdiff_angle_gamma         119.930(8)
_cell_oxdiff_volume              10451(1)

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R -3 '
_symmetry_space_group_name_Hall  '-R 3'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/3,y+2/3,z+2/3
-x+1/3,-y+2/3,-z+2/3
x+2/3,y+1/3,z+1/3
-x+2/3,-y+1/3,-z+1/3
y,-x+y,-z
-y,x-y,z
y+1/3,-x+y+2/3,-z+2/3
-y+1/3,x-y+2/3,z+2/3
y+2/3,-x+y+1/3,-z+1/3
-y+2/3,x-y+1/3,z+1/3
-x+y,-x,z
x-y,x,-z
-x+y+1/3,-x+2/3,z+2/3
x-y+1/3,x+2/3,-z+2/3
-x+y+2/3,-x+1/3,z+1/3
x-y+2/3,x+1/3,-z+1/3

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            18

_chemical_formula_sum            'C29.166 H31.25 N1.08'
_chemical_formula_moiety         'C29 H31 N, 0.0833(H3 C2 N)'
_chemical_compound_source        ?
_chemical_formula_weight         396.94


_cell_measurement_temperature    175

_exptl_crystal_description       stick
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_max          0.400
_exptl_absorpt_correction_T_min  0.34134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             3848.508
_exptl_absorpt_coefficient_mu    0.065
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       1.04
_montpellier_reflns_completeness_maxres 99.09
_montpellier_reflns_redundancy_maxres 4.44

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.63 5.5 18.17 0.042 96.5 96.46
1 1.63 1.30 4.6 5.54 0.139 100.0 98.20
2 1.30 1.13 4.1 4.73 0.146 100.0 98.79
3 1.13 1.04 3.6 2.96 0.242 100.0 99.09
4 1.04 0.96 3.2 1.90 0.374 100.0 99.27
5 0.96 0.90 3.1 1.43 0.468 100.0 99.39
6 0.90 0.86 2.9 0.97 0.616 100.0 99.48
7 0.86 0.82 2.5 0.76 0.640 100.0 99.54
8 0.82 0.79 2.3 0.56 0.668 94.9 99.01
9 0.79 0.73 1.5 0.62 0.834 45.7 88.68
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      -0.0029066000
_diffrn_orient_matrix_UB_12      0.0119414000
_diffrn_orient_matrix_UB_13      0.0576378000
_diffrn_orient_matrix_UB_21      -0.0172069000
_diffrn_orient_matrix_UB_22      -0.0096424000
_diffrn_orient_matrix_UB_23      -0.0275566000
_diffrn_orient_matrix_UB_31      -0.0028175000
_diffrn_orient_matrix_UB_32      -0.0087756000
_diffrn_orient_matrix_UB_33      0.1086810000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   33.50   0.7500   75.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6287 -101.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00   28.50   0.7500   75.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6287  -88.0000 -118.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   22.50   0.7500   75.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6287   77.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   87.00   0.7500   75.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6287   77.0000  -30.0000 132

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            18106
_reflns_number_total             5450
_diffrn_reflns_av_R_equivalents  0.132
_diffrn_reflns_av_unetI/netI     0.4091
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5450 
# Theoretical number of reflections is about 11358 


_diffrn_reflns_theta_min         4.153
_diffrn_reflns_theta_max         28.917
_diffrn_measured_fraction_theta_max 0.887

_diffrn_reflns_theta_full        25.158
_diffrn_measured_fraction_theta_full 0.967


_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_h_max       61
_diffrn_reflns_limit_k_min       -61
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -58
_reflns_limit_h_max              28
_reflns_limit_k_min              0
_reflns_limit_k_max              61
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   1.34
_oxford_diffrn_Wilson_scale      29.76

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.34


# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold


# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     0
_refine_ls_number_parameters     278
_oxford_refine_ls_R_factor_ref   0.0713
_refine_ls_wR_factor_ref         0.0424
_refine_ls_goodness_of_fit_ref   1.1478
_refine_ls_shift/su_max          0.0058815
_refine_ls_shift/su_mean         0.0001963


# The values computed with all filters except I/sigma
_oxford_reflns_number_all        5442
_refine_ls_R_factor_all          0.2244
_refine_ls_wR_factor_all         0.0893

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2119
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_gt          0.0424

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 1.74 -9.13 -1.29 -2.61 -1.97 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.3333 0.6667 0.1667 0.0603 0.5000 Uani S T . . . .
C2 C 0.3333 0.6667 -0.037(6) 0.0464 0.2500 Uani S T . . . .
C3 C 0.3333 0.6667 -0.3333 0.1853 0.5000 Uani S T . . . .
N4 N 0.36772(7) 0.52838(7) 0.5464(5) 0.0400 1.0000 Uani . . . . . .
C5 C 0.38931(8) 0.52354(8) 0.7011(6) 0.0356 1.0000 Uani . . . . . .
C6 C 0.40005(8) 0.54226(8) 0.9065(6) 0.0417 1.0000 Uani . . . . . .
C7 C 0.42208(9) 0.53954(9) 1.0577(6) 0.0451 1.0000 Uani . . . . . .
C8 C 0.43477(8) 0.51893(8) 1.0066(6) 0.0370 1.0000 Uani . . . . . .
C9 C 0.46007(8) 0.51733(9) 1.1682(6) 0.0440 1.0000 Uani . . . . . .
C10 C 0.49571(8) 0.54546(9) 1.1321(6) 0.0413 1.0000 Uani . . . . . .
C11 C 0.51918(8) 0.54515(8) 1.3196(6) 0.0402 1.0000 Uani . . . . . .
C12 C 0.55558(8) 0.57144(8) 1.2874(6) 0.0419 1.0000 Uani . . . . . .
C13 C 0.57698(8) 0.57337(9) 1.4991(6) 0.0444 1.0000 Uani . . . . . .
C14 C 0.61411(9) 0.59651(10) 1.4667(7) 0.0531 1.0000 Uani . . . . . .
C15 C 0.63510(10) 0.59591(10) 1.6687(8) 0.0639 1.0000 Uani . . . . . .
C16 C 0.67191(11) 0.62099(13) 1.6403(9) 0.0882 1.0000 Uani . . . . . .
H162 H 0.6843 0.6183 1.7680 0.1309 1.0000 Uiso R . . . . .
H163 H 0.6753 0.6435 1.6423 0.1311 1.0000 Uiso R . . . . .
H161 H 0.6794 0.6171 1.4912 0.1312 1.0000 Uiso R . . . . .
H152 H 0.6274 0.6012 1.8147 0.0751 1.0000 Uiso R . . . . .
H151 H 0.6318 0.5736 1.6840 0.0749 1.0000 Uiso R . . . . .
H142 H 0.6177 0.6192 1.4509 0.0621 1.0000 Uiso R . . . . .
H141 H 0.6212 0.5904 1.3197 0.0624 1.0000 Uiso R . . . . .
H131 H 0.5701 0.5807 1.6369 0.0516 1.0000 Uiso R . . . . .
H132 H 0.5731 0.5510 1.5295 0.0517 1.0000 Uiso R . . . . .
H121 H 0.5573 0.5932 1.2696 0.0491 1.0000 Uiso R . . . . .
H122 H 0.5638 0.5662 1.1437 0.0491 1.0000 Uiso R . . . . .
H111 H 0.5117 0.5492 1.4706 0.0460 1.0000 Uiso R . . . . .
H112 H 0.5170 0.5230 1.3201 0.0466 1.0000 Uiso R . . . . .
H101 H 0.4965 0.5670 1.1386 0.0476 1.0000 Uiso R . . . . .
H102 H 0.5031 0.5430 0.9744 0.0478 1.0000 Uiso R . . . . .
H91 H 0.4538 0.5176 1.3317 0.0505 1.0000 Uiso R . . . . .
H92 H 0.4597 0.4966 1.1378 0.0510 1.0000 Uiso R . . . . .
C17 C 0.42394(9) 0.50023(9) 0.8017(6) 0.0448 1.0000 Uani . . . . . .
C18 C 0.40144(8) 0.50239(8) 0.6504(6) 0.0402 1.0000 Uani . . . . . .
H181 H 0.3948 0.4901 0.5095 0.0470 1.0000 Uiso R . . . . .
H171 H 0.4316 0.4855 0.7652 0.0517 1.0000 Uiso R . . . . .
H71 H 0.4284 0.5519 1.2003 0.0519 1.0000 Uiso R . . . . .
H61 H 0.3923 0.5572 0.9398 0.0488 1.0000 Uiso R . . . . .
C19 C 0.34533(8) 0.50300(9) 0.4350(6) 0.0390 1.0000 Uani . . . . . .
C20 C 0.32209(8) 0.50376(8) 0.2608(6) 0.0400 1.0000 Uani . . . . . .
C21 C 0.30986(8) 0.52640(9) 0.2783(6) 0.0419 1.0000 Uani . . . . . .
C22 C 0.31743(9) 0.54929(9) 0.4671(7) 0.0491 1.0000 Uani . . . . . .
C23 C 0.30457(9) 0.57024(10) 0.4733(8) 0.0562 1.0000 Uani . . . . . .
C24 C 0.28329(9) 0.56959(11) 0.2883(9) 0.0595 1.0000 Uani . . . . . .
C25 C 0.27494(9) 0.54760(11) 0.1109(8) 0.0587 1.0000 Uani . . . . . .
C26 C 0.28709(8) 0.52509(10) 0.0980(7) 0.0469 1.0000 Uani . . . . . .
C27 C 0.27626(9) 0.50096(10) -0.0797(7) 0.0542 1.0000 Uani . . . . . .
C28 C 0.28673(8) 0.47801(9) -0.0932(6) 0.0450 1.0000 Uani . . . . . .
C29 C 0.31077(8) 0.47971(9) 0.0752(6) 0.0430 1.0000 Uani . . . . . .
C30 C 0.32257(9) 0.45678(9) 0.0414(7) 0.0506 1.0000 Uani . . . . . .
C31 C 0.31051(10) 0.43344(10) -0.1337(7) 0.0594 1.0000 Uani . . . . . .
C32 C 0.28573(10) 0.43095(11) -0.2919(8) 0.0605 1.0000 Uani . . . . . .
C33 C 0.27446(9) 0.45238(10) -0.2726(7) 0.0583 1.0000 Uani . . . . . .
H331 H 0.2582 0.4513 -0.3777 0.0677 1.0000 Uiso R . . . . .
H321 H 0.2772 0.4142 -0.4108 0.0721 1.0000 Uiso R . . . . .
H311 H 0.3186 0.4186 -0.1474 0.0707 1.0000 Uiso R . . . . .
H301 H 0.3393 0.4583 0.1410 0.0597 1.0000 Uiso R . . . . .
H271 H 0.2611 0.5000 -0.1929 0.0632 1.0000 Uiso R . . . . .
H251 H 0.2604 0.5474 -0.0097 0.0688 1.0000 Uiso R . . . . .
H241 H 0.2749 0.5845 0.2957 0.0716 1.0000 Uiso R . . . . .
H231 H 0.3099 0.5850 0.6013 0.0656 1.0000 Uiso R . . . . .
H221 H 0.3316 0.5503 0.5883 0.0565 1.0000 Uiso R . . . . .
H191 H 0.3429 0.4815 0.4674 0.0448 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4137(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 6_565 1.15(4) yes
N1 . C2 . 1.15(4) yes
C2 . C3 . 1.67(4) yes
N4 . C5 . 1.426(4) yes
N4 . C19 . 1.277(4) yes
C5 . C6 . 1.380(5) yes
C5 . C18 . 1.381(4) yes
C6 . C7 . 1.382(5) yes
C6 . H61 . 0.945 no
C7 . C8 . 1.378(5) yes
C7 . H71 . 0.943 no
C8 . C9 . 1.514(5) yes
C8 . C17 . 1.377(4) yes
C9 . C10 . 1.521(4) yes
C9 . H91 . 0.967 no
C9 . H92 . 0.967 no
C10 . C11 . 1.520(4) yes
C10 . H101 . 0.980 no
C10 . H102 . 0.978 no
C11 . C12 . 1.518(4) yes
C11 . H111 . 0.970 no
C11 . H112 . 0.977 no
C12 . C13 . 1.523(5) yes
C12 . H121 . 0.976 no
C12 . H122 . 0.975 no
C13 . C14 . 1.515(5) yes
C13 . H131 . 0.962 no
C13 . H132 . 0.975 no
C14 . C15 . 1.505(5) yes
C14 . H142 . 0.983 no
C14 . H141 . 0.982 no
C15 . C16 . 1.517(6) yes
C15 . H152 . 0.973 no
C15 . H151 . 0.968 no
C16 . H162 . 0.966 no
C16 . H163 . 0.974 no
C16 . H161 . 0.958 no
C17 . C18 . 1.387(5) yes
C17 . H171 . 0.936 no
C18 . H181 . 0.935 no
C19 . C20 . 1.469(5) yes
C19 . H191 . 0.960 no
C20 . C21 . 1.423(5) yes
C20 . C29 . 1.422(5) yes
C21 . C22 . 1.415(5) yes
C21 . C26 . 1.442(5) yes
C22 . C23 . 1.370(5) yes
C22 . H221 . 0.932 no
C23 . C24 . 1.423(6) yes
C23 . H231 . 0.938 no
C24 . C25 . 1.338(6) yes
C24 . H241 . 0.948 no
C25 . C26 . 1.413(5) yes
C25 . H251 . 0.953 no
C26 . C27 . 1.393(5) yes
C27 . C28 . 1.373(5) yes
C27 . H271 . 0.932 no
C28 . C29 . 1.433(5) yes
C28 . C33 . 1.441(5) yes
C29 . C30 . 1.429(5) yes
C30 . C31 . 1.360(5) yes
C30 . H301 . 0.931 no
C31 . C32 . 1.411(5) yes
C31 . H311 . 0.934 no
C32 . C33 . 1.337(6) yes
C32 . H321 . 0.948 no
C33 . H331 . 0.938 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 6_565 N1 . C2 . 179.990 yes
N1 . C2 . C3 . 179.993 yes
C2 18_554 C3 . C2 . 179.993 yes
C5 . N4 . C19 . 117.7(3) yes
N4 . C5 . C6 . 118.3(3) yes
N4 . C5 . C18 . 123.5(3) yes
C6 . C5 . C18 . 118.2(3) yes
C5 . C6 . C7 . 120.6(3) yes
C5 . C6 . H61 . 118.5 no
C7 . C6 . H61 . 120.9 no
C6 . C7 . C8 . 121.6(3) yes
C6 . C7 . H71 . 119.2 no
C8 . C7 . H71 . 119.2 no
C7 . C8 . C9 . 121.1(3) yes
C7 . C8 . C17 . 117.6(3) yes
C9 . C8 . C17 . 121.3(3) yes
C8 . C9 . C10 . 114.4(3) yes
C8 . C9 . H91 . 109.0 no
C10 . C9 . H91 . 108.8 no
C8 . C9 . H92 . 108.2 no
C10 . C9 . H92 . 107.4 no
H91 . C9 . H92 . 108.9 no
C9 . C10 . C11 . 112.0(3) yes
C9 . C10 . H101 . 109.7 no
C11 . C10 . H101 . 108.7 no
C9 . C10 . H102 . 108.4 no
C11 . C10 . H102 . 109.6 no
H101 . C10 . H102 . 108.4 no
C10 . C11 . C12 . 115.0(3) yes
C10 . C11 . H111 . 106.3 no
C12 . C11 . H111 . 108.0 no
C10 . C11 . H112 . 108.1 no
C12 . C11 . H112 . 109.5 no
H111 . C11 . H112 . 109.8 no
C11 . C12 . C13 . 112.5(3) yes
C11 . C12 . H121 . 109.0 no
C13 . C12 . H121 . 107.8 no
C11 . C12 . H122 . 108.3 no
C13 . C12 . H122 . 109.9 no
H121 . C12 . H122 . 109.4 no
C12 . C13 . C14 . 115.0(3) yes
C12 . C13 . H131 . 109.3 no
C14 . C13 . H131 . 107.8 no
C12 . C13 . H132 . 107.8 no
C14 . C13 . H132 . 108.3 no
H131 . C13 . H132 . 108.5 no
C13 . C14 . C15 . 114.3(3) yes
C13 . C14 . H142 . 107.1 no
C15 . C14 . H142 . 108.8 no
C13 . C14 . H141 . 108.7 no
C15 . C14 . H141 . 108.6 no
H142 . C14 . H141 . 109.2 no
C14 . C15 . C16 . 113.3(4) yes
C14 . C15 . H152 . 108.3 no
C16 . C15 . H152 . 107.9 no
C14 . C15 . H151 . 109.1 no
C16 . C15 . H151 . 110.2 no
H152 . C15 . H151 . 107.9 no
C15 . C16 . H162 . 109.6 no
C15 . C16 . H163 . 109.6 no
H162 . C16 . H163 . 110.0 no
C15 . C16 . H161 . 108.7 no
H162 . C16 . H161 . 109.6 no
H163 . C16 . H161 . 109.3 no
C8 . C17 . C18 . 121.3(3) yes
C8 . C17 . H171 . 119.4 no
C18 . C17 . H171 . 119.4 no
C17 . C18 . C5 . 120.7(3) yes
C17 . C18 . H181 . 120.4 no
C5 . C18 . H181 . 118.8 no
N4 . C19 . C20 . 124.9(3) yes
N4 . C19 . H191 . 118.7 no
C20 . C19 . H191 . 116.3 no
C19 . C20 . C21 . 122.5(3) yes
C19 . C20 . C29 . 117.3(3) yes
C21 . C20 . C29 . 120.1(3) yes
C20 . C21 . C22 . 124.3(3) yes
C20 . C21 . C26 . 118.2(3) yes
C22 . C21 . C26 . 117.5(3) yes
C21 . C22 . C23 . 121.1(4) yes
C21 . C22 . H221 . 119.4 no
C23 . C22 . H221 . 119.5 no
C22 . C23 . C24 . 120.5(4) yes
C22 . C23 . H231 . 119.3 no
C24 . C23 . H231 . 120.2 no
C23 . C24 . C25 . 119.7(4) yes
C23 . C24 . H241 . 119.0 no
C25 . C24 . H241 . 121.2 no
C24 . C25 . C26 . 122.0(4) yes
C24 . C25 . H251 . 118.3 no
C26 . C25 . H251 . 119.7 no
C21 . C26 . C25 . 119.0(4) yes
C21 . C26 . C27 . 120.1(4) yes
C25 . C26 . C27 . 120.8(4) yes
C26 . C27 . C28 . 122.4(4) yes
C26 . C27 . H271 . 119.3 no
C28 . C27 . H271 . 118.3 no
C27 . C28 . C29 . 119.1(4) yes
C27 . C28 . C33 . 122.0(4) yes
C29 . C28 . C33 . 118.9(4) yes
C28 . C29 . C20 . 120.0(3) yes
C28 . C29 . C30 . 116.5(4) yes
C20 . C29 . C30 . 123.4(3) yes
C29 . C30 . C31 . 122.0(4) yes
C29 . C30 . H301 . 118.6 no
C31 . C30 . H301 . 119.4 no
C30 . C31 . C32 . 121.1(4) yes
C30 . C31 . H311 . 119.2 no
C32 . C31 . H311 . 119.7 no
C31 . C32 . C33 . 119.5(4) yes
C31 . C32 . H321 . 120.2 no
C33 . C32 . H321 . 120.3 no
C28 . C33 . C32 . 121.9(4) yes
C28 . C33 . H331 . 117.5 no
C32 . C33 . H331 . 120.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C22 . H221 . N4 . 122.60(12) 0.932 2.362 2.969(6) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
25 27 4 x .
-20 18 7 x .
-54 42 3 x .
-23 12 7 x .
-22 19 7 x .
-37 23 6 x .
-36 24 6 x .
-53 50 2 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9
_database_code_depnum_ccdc_archive 'CCDC 1058506'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
_cell_length_a                   8.2148(3)
_cell_length_b                   9.5771(3)
_cell_length_c                   12.8008(5)
_cell_angle_alpha                73.643(3)
_cell_angle_beta                 73.317(3)
_cell_angle_gamma                89.653(3)
_cell_volume                     922.58(6)
_cell_measurement_reflns_used    9040
_cell_measurement_theta_min      4.2760
_cell_measurement_theta_max      37.0600
_cell_oxdiff_length_a            8.2073(3)
_cell_oxdiff_length_b            9.5714(3)
_cell_oxdiff_length_c            12.7910(4)
_cell_oxdiff_angle_alpha         73.613(3)
_cell_oxdiff_angle_beta          73.308(3)
_cell_oxdiff_angle_gamma         89.655(3)
_cell_oxdiff_volume              920.28(5)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C25 H23 N'
_chemical_formula_moiety         'C25 H23 N'
_chemical_compound_source        ?
_chemical_formula_weight         337.44


_cell_measurement_temperature    175

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_max          0.400
_exptl_absorpt_correction_T_min  0.98425
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.070
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.58
_montpellier_reflns_completeness_maxres 96.55
_montpellier_reflns_redundancy_maxres 4.84

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.27 7.1 98.00 0.011 98.3 98.31
1 1.27 1.01 6.7 41.53 0.022 100.0 99.15
2 1.01 0.88 5.9 19.22 0.044 100.0 99.43
3 0.88 0.80 5.3 12.12 0.073 100.0 99.57
4 0.80 0.74 4.8 9.12 0.106 100.0 99.66
5 0.74 0.70 4.4 7.65 0.116 100.0 99.71
6 0.70 0.67 4.1 5.91 0.149 100.0 99.76
7 0.67 0.64 3.8 4.17 0.208 100.0 99.79
8 0.64 0.61 3.6 3.01 0.304 100.0 99.81
9 0.61 0.58 2.7 3.00 0.274 74.7 96.55
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      0.0320918000
_diffrn_orient_matrix_UB_12      -0.0645528000
_diffrn_orient_matrix_UB_13      0.0274408000
_diffrn_orient_matrix_UB_21      0.0809611000
_diffrn_orient_matrix_UB_22      0.0384584000
_diffrn_orient_matrix_UB_23      -0.0152219000
_diffrn_orient_matrix_UB_31      -0.0247120000
_diffrn_orient_matrix_UB_32      0.0189888000
_diffrn_orient_matrix_UB_33      0.0517777000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   77.00  108.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125  179.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega    9.00   44.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125   77.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega   74.00  101.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   43.00  105.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125   38.0000 -120.0000 62

#__ type_ start__ end____ width___ exp.time_
  5 omega   62.00   99.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125   38.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
  6 omega    4.00   99.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125 -130.0000  -40.0000 95

#__ type_ start__ end____ width___ exp.time_
  7 omega   16.00   95.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125   41.0000  105.0000 79

#__ type_ start__ end____ width___ exp.time_
  8 omega   10.00   99.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125   77.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00  111.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125  179.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
 10 omega    8.00  108.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125   77.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
 11 omega    8.00  108.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125   77.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
 12 omega  -34.00   64.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125  -38.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
 13 omega  -34.00   64.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125  -38.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
 14 omega -115.00  -53.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -      -38.7938  179.0000   30.0000 62

#__ type_ start__ end____ width___ exp.time_
 15 omega  -39.00   -3.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -      -38.7938  -88.0000   38.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega -115.00  -53.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -      -38.7938  179.0000  -30.0000 62

#__ type_ start__ end____ width___ exp.time_
 17 omega    8.00  108.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125   77.0000  150.0000 100

#__ type_ start__ end____ width___ exp.time_
 18 omega  -34.00   64.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125  -38.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
 19 omega   13.00  110.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -       38.0125   38.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
 20 omega -115.00  -53.00   1.0000   12.1100
omega____ theta____ kappa____ phi______ frames
    -      -38.7938  179.0000 -150.0000 62

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            45049
_reflns_number_total             9316
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.0414
# Number of reflections without Friedels Law is 9341
# Number of reflections with Friedels Law is 9316
# Theoretical number of reflections is about 9635


_diffrn_reflns_theta_min         4.278
_diffrn_reflns_theta_max         37.381
_diffrn_measured_fraction_theta_max 0.966

_diffrn_reflns_theta_full        35.138
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -13
_reflns_limit_h_max              14
_reflns_limit_k_min              -15
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.20
_refine_diff_density_max         0.51


# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         6335
_refine_ls_number_restraints     18
_refine_ls_number_parameters     263
_oxford_refine_ls_R_factor_ref   0.0630
_refine_ls_wR_factor_ref         0.0682
_refine_ls_goodness_of_fit_ref   1.0521
_refine_ls_shift/su_max          0.0006980
_refine_ls_shift/su_mean         0.0000403


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        9316
_refine_ls_R_factor_all          0.0941
_refine_ls_wR_factor_all         0.0737

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6335
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_gt          0.0682

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 8.83 1.84 5.45 -0.392 -1.72 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 1.12031(10) 0.18139(9) 0.21878(7) 0.0293 1.0000 Uani . . . . . .
C2 C 0.97862(11) 0.15661(9) 0.20191(7) 0.0273 1.0000 Uani . . . . . .
C3 C 0.88805(10) 0.27286(9) 0.14470(7) 0.0242 1.0000 Uani . . . . . .
C4 C 0.81186(10) 0.24432(9) 0.06583(7) 0.0240 1.0000 Uani . . . . . .
C5 C 0.73290(10) 0.35851(9) 0.00292(7) 0.0266 1.0000 Uani . . . . . .
C6 C 0.72923(12) 0.49525(10) 0.02174(8) 0.0299 1.0000 Uani . . . . . .
C7 C 0.79654(11) 0.52275(9) 0.10305(7) 0.0274 1.0000 Uani . . . . . .
C8 C 0.87831(10) 0.41098(9) 0.16581(7) 0.0253 1.0000 Uani . . . . . .
C9 C 0.94263(13) 0.44388(11) 0.24946(8) 0.0321 1.0000 Uani . . . . . .
C10 C 0.92716(14) 0.57766(12) 0.26842(9) 0.0377 1.0000 Uani . . . . . .
C11 C 0.84766(15) 0.68792(11) 0.20532(10) 0.0396 1.0000 Uani . . . . . .
C12 C 0.78425(14) 0.66143(10) 0.12510(9) 0.0357 1.0000 Uani . . . . . .
C13 C 0.66121(13) 0.33146(12) -0.07971(9) 0.0352 1.0000 Uani . . . . . .
C14 C 0.66395(14) 0.19857(13) -0.09828(9) 0.0391 1.0000 Uani . . . . . .
C15 C 0.74140(13) 0.08490(12) -0.03654(9) 0.0355 1.0000 Uani . . . . . .
C16 C 0.81457(12) 0.10726(10) 0.04145(8) 0.0295 1.0000 Uani . . . . . .
C17 C 1.19539(11) 0.06380(10) 0.27827(7) 0.0273 1.0000 Uani . . . . . .
C18 C 1.37298(11) 0.06821(10) 0.24560(8) 0.0304 1.0000 Uani . . . . . .
C19 C 1.45463(11) -0.04158(11) 0.30265(8) 0.0312 1.0000 Uani . . . . . .
C20 C 1.36330(12) -0.15732(11) 0.39411(8) 0.0306 1.0000 Uani . . . . . .
C21 C 1.45140(14) -0.27271(11) 0.46024(9) 0.0358 1.0000 Uani . . . . . .
C25 C 1.18622(14) -0.16069(13) 0.42600(9) 0.0421 1.0000 Uani . . . . . .
C26 C 1.10230(13) -0.05188(13) 0.36967(9) 0.0397 1.0000 Uani . . . . . .
H21 H 0.9292 0.0606 0.2251 0.0289 1.0000 Uiso R . . . . .
H61 H 0.6830 0.5700 -0.0218 0.0333 1.0000 Uiso R . . . . .
H91 H 0.9942 0.3739 0.2921 0.0354 1.0000 Uiso R . . . . .
H101 H 0.9678 0.6006 0.3229 0.0419 1.0000 Uiso R . . . . .
H111 H 0.8387 0.7797 0.2177 0.0439 1.0000 Uiso R . . . . .
H121 H 0.7324 0.7350 0.0811 0.0380 1.0000 Uiso R . . . . .
H131 H 0.6147 0.4064 -0.1204 0.0384 1.0000 Uiso R . . . . .
H141 H 0.6178 0.1859 -0.1542 0.0435 1.0000 Uiso R . . . . .
H151 H 0.7433 -0.0091 -0.0473 0.0391 1.0000 Uiso R . . . . .
H161 H 0.8684 0.0311 0.0767 0.0323 1.0000 Uiso R . . . . .
H181 H 1.4366 0.1448 0.1860 0.0321 1.0000 Uiso R . . . . .
H191 H 1.5739 -0.0367 0.2778 0.0335 1.0000 Uiso R . . . . .
H251 H 1.1234 -0.2362 0.4873 0.0473 1.0000 Uiso R . . . . .
H261 H 0.9816 -0.0562 0.3947 0.0429 1.0000 Uiso R . . . . .
C22 C 1.47290(16) -0.23828(13) 0.56559(9) 0.0309 0.809(3) Uani . U P 1 1 .
C23 C 1.54684(17) -0.35932(15) 0.64000(10) 0.0334 0.809(3) Uani . U P 1 1 .
C24 C 1.73192(19) -0.3768(2) 0.58574(14) 0.0493 0.809(3) Uani . U P 1 1 .
C221 C 1.5890(8) -0.1927(6) 0.4979(5) 0.0377 0.191(3) Uani . U P 1 2 .
C231 C 1.6974(7) -0.3024(7) 0.5520(5) 0.0389 0.191(3) Uani . U P 1 2 .
C241 C 1.5970(10) -0.4134(8) 0.6622(6) 0.0482 0.191(3) Uani . U P 1 2 .
H221 H 1.5466 -0.1517 0.5410 0.0313 0.809(3) Uiso R . P 1 1 .
H222 H 1.3640 -0.2226 0.6103 0.0313 0.809(3) Uiso R . P 1 1 .
H2211 H 1.6587 -0.1197 0.4338 0.0455 0.191(3) Uiso R . P 1 2 .
H2212 H 1.5275 -0.1485 0.5536 0.0455 0.191(3) Uiso R . P 1 2 .
H231 H 1.5368 -0.3376 0.7094 0.0345 0.809(3) Uiso R . P 1 1 .
H232 H 1.4825 -0.4488 0.6556 0.0345 0.809(3) Uiso R . P 1 1 .
H2311 H 1.7828 -0.2511 0.5667 0.0530 0.191(3) Uiso R . P 1 2 .
H2312 H 1.7499 -0.3537 0.4991 0.0530 0.191(3) Uiso R . P 1 2 .
H241 H 1.7698 -0.4536 0.6364 0.0548 0.809(3) Uiso R . P 1 1 .
H242 H 1.7984 -0.2885 0.5704 0.0548 0.809(3) Uiso R . P 1 1 .
H243 H 1.7440 -0.3997 0.5165 0.0548 0.809(3) Uiso R . P 1 1 .
H2411 H 1.6697 -0.4801 0.6923 0.0689 0.191(3) Uiso R . P 1 2 .
H2412 H 1.5446 -0.3627 0.7155 0.0689 0.191(3) Uiso R . P 1 2 .
H2413 H 1.5117 -0.4653 0.6479 0.0689 0.191(3) Uiso R . P 1 2 .
H211 H 1.5611 -0.2791 0.4116 0.0374 0.809(3) Uiso R . P 1 1 .
H212 H 1.3862 -0.3638 0.4840 0.0374 0.809(3) Uiso R . P 1 1 .
H213 H 1.5108 -0.3287 0.4130 0.0374 0.191(3) Uiso R . P 1 2 .
H214 H 1.3698 -0.3350 0.5252 0.0374 0.191(3) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          8.426(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.2784(11) yes
N1 . C17 . 1.4166(11) yes
C2 . C3 . 1.4740(11) yes
C2 . H21 . 0.938 no
C3 . C4 . 1.4164(12) yes
C3 . C8 . 1.4202(11) yes
C4 . C5 . 1.4354(11) yes
C4 . C16 . 1.4309(12) yes
C5 . C6 . 1.3953(13) yes
C5 . C13 . 1.4306(13) yes
C6 . C7 . 1.3947(13) yes
C6 . H61 . 0.928 no
C7 . C8 . 1.4350(12) yes
C7 . C12 . 1.4307(12) yes
C8 . C9 . 1.4289(13) yes
C9 . C10 . 1.3682(14) yes
C9 . H91 . 0.922 no
C10 . C11 . 1.4171(17) yes
C10 . H101 . 0.931 no
C11 . C12 . 1.3585(17) yes
C11 . H111 . 0.935 no
C12 . H121 . 0.952 no
C13 . C14 . 1.3579(16) yes
C13 . H131 . 0.912 no
C14 . C15 . 1.4178(15) yes
C14 . H141 . 0.936 no
C15 . C16 . 1.3676(13) yes
C15 . H151 . 0.948 no
C16 . H161 . 0.926 no
C17 . C18 . 1.3948(12) yes
C17 . C26 . 1.3955(13) yes
C18 . C19 . 1.3889(13) yes
C18 . H181 . 0.924 no
C19 . C20 . 1.3918(14) yes
C19 . H191 . 0.936 no
C20 . C21 . 1.5089(12) yes
C20 . C25 . 1.3914(14) yes
C21 . C22 . 1.5319(15) yes
C21 . H211 . 0.950 no
C21 . H212 . 0.950 no
C21 . C221 . 1.621(5) yes
C21 . H213 . 0.950 no
C21 . H214 . 0.950 no
C25 . C26 . 1.3910(14) yes
C25 . H251 . 0.926 no
C26 . H261 . 0.948 no
C22 . C23 . 1.5237(17) yes
C22 . H221 . 0.950 no
C22 . H222 . 0.950 no
C23 . C24 . 1.509(2) yes
C23 . H231 . 0.950 no
C23 . H232 . 0.950 no
C24 . H241 . 0.950 no
C24 . H242 . 0.950 no
C24 . H243 . 0.950 no
C221 . C231 . 1.520(7) yes
C221 . H2211 . 0.950 no
C221 . H2212 . 0.950 no
C231 . C241 . 1.516(9) yes
C231 . H2311 . 0.950 no
C231 . H2312 . 0.950 no
C241 . H2411 . 0.950 no
C241 . H2412 . 0.950 no
C241 . H2413 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C17 . 119.19(8) yes
N1 . C2 . C3 . 122.96(8) yes
N1 . C2 . H21 . 119.8 no
C3 . C2 . H21 . 117.3 no
C2 . C3 . C4 . 118.15(7) yes
C2 . C3 . C8 . 121.66(7) yes
C4 . C3 . C8 . 120.18(7) yes
C3 . C4 . C5 . 119.49(7) yes
C3 . C4 . C16 . 123.27(7) yes
C5 . C4 . C16 . 117.20(8) yes
C4 . C5 . C6 . 119.68(8) yes
C4 . C5 . C13 . 119.58(8) yes
C6 . C5 . C13 . 120.73(8) yes
C5 . C6 . C7 . 121.42(8) yes
C5 . C6 . H61 . 119.3 no
C7 . C6 . H61 . 119.2 no
C6 . C7 . C8 . 119.88(8) yes
C6 . C7 . C12 . 120.65(8) yes
C8 . C7 . C12 . 119.47(9) yes
C7 . C8 . C3 . 119.23(8) yes
C7 . C8 . C9 . 117.68(8) yes
C3 . C8 . C9 . 123.06(8) yes
C8 . C9 . C10 . 120.96(9) yes
C8 . C9 . H91 . 119.8 no
C10 . C9 . H91 . 119.2 no
C9 . C10 . C11 . 121.00(10) yes
C9 . C10 . H101 . 122.0 no
C11 . C10 . H101 . 117.0 no
C10 . C11 . C12 . 120.09(9) yes
C10 . C11 . H111 . 120.8 no
C12 . C11 . H111 . 119.1 no
C7 . C12 . C11 . 120.79(10) yes
C7 . C12 . H121 . 118.2 no
C11 . C12 . H121 . 121.0 no
C5 . C13 . C14 . 121.06(9) yes
C5 . C13 . H131 . 118.2 no
C14 . C13 . H131 . 120.7 no
C13 . C14 . C15 . 119.85(9) yes
C13 . C14 . H141 . 118.4 no
C15 . C14 . H141 . 121.7 no
C14 . C15 . C16 . 120.89(9) yes
C14 . C15 . H151 . 121.3 no
C16 . C15 . H151 . 117.8 no
C4 . C16 . C15 . 121.39(8) yes
C4 . C16 . H161 . 121.1 no
C15 . C16 . H161 . 117.5 no
N1 . C17 . C18 . 117.44(8) yes
N1 . C17 . C26 . 123.79(8) yes
C18 . C17 . C26 . 118.73(8) yes
C17 . C18 . C19 . 120.30(8) yes
C17 . C18 . H181 . 119.8 no
C19 . C18 . H181 . 119.9 no
C18 . C19 . C20 . 121.53(8) yes
C18 . C19 . H191 . 118.4 no
C20 . C19 . H191 . 120.1 no
C19 . C20 . C21 . 121.76(9) yes
C19 . C20 . C25 . 117.70(8) yes
C21 . C20 . C25 . 120.49(9) yes
C20 . C21 . C22 . 112.57(8) yes
C20 . C21 . H211 . 108.5 no
C22 . C21 . H211 . 108.5 no
C20 . C21 . H212 . 108.9 no
C22 . C21 . H212 . 108.8 no
H211 . C21 . H212 . 109.5 no
C20 . C21 . C221 . 108.6(2) yes
C20 . C21 . H213 . 109.6 no
C221 . C21 . H213 . 108.4 no
C20 . C21 . H214 . 110.0 no
C221 . C21 . H214 . 110.7 no
H213 . C21 . H214 . 109.5 no
C20 . C25 . C26 . 121.54(9) yes
C20 . C25 . H251 . 118.9 no
C26 . C25 . H251 . 119.6 no
C17 . C26 . C25 . 120.19(9) yes
C17 . C26 . H261 . 120.4 no
C25 . C26 . H261 . 119.4 no
C21 . C22 . C23 . 113.78(9) yes
C21 . C22 . H221 . 108.5 no
C23 . C22 . H221 . 108.5 no
C21 . C22 . H222 . 108.2 no
C23 . C22 . H222 . 108.4 no
H221 . C22 . H222 . 109.5 no
C22 . C23 . C24 . 113.62(11) yes
C22 . C23 . H231 . 108.3 no
C24 . C23 . H231 . 108.4 no
C22 . C23 . H232 . 108.4 no
C24 . C23 . H232 . 108.5 no
H231 . C23 . H232 . 109.5 no
C23 . C24 . H241 . 109.3 no
C23 . C24 . H242 . 109.6 no
H241 . C24 . H242 . 109.5 no
C23 . C24 . H243 . 109.5 no
H241 . C24 . H243 . 109.5 no
H242 . C24 . H243 . 109.5 no
C21 . C221 . C231 . 111.1(4) yes
C21 . C221 . H2211 . 110.0 no
C231 . C221 . H2211 . 110.7 no
C21 . C221 . H2212 . 107.8 no
C231 . C221 . H2212 . 107.9 no
H2211 . C221 . H2212 . 109.5 no
C221 . C231 . C241 . 113.8(5) yes
C221 . C231 . H2311 . 108.8 no
C241 . C231 . H2311 . 108.8 no
C221 . C231 . H2312 . 107.9 no
C241 . C231 . H2312 . 108.1 no
H2311 . C231 . H2312 . 109.5 no
C231 . C241 . H2411 . 110.8 no
C231 . C241 . H2412 . 108.5 no
H2411 . C241 . H2412 . 109.5 no
C231 . C241 . H2413 . 109.1 no
H2411 . C241 . H2413 . 109.5 no
H2412 . C241 . H2413 . 109.5 no


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14
_database_code_depnum_ccdc_archive 'CCDC 1058507'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_exptl_special_details           
;
 The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
_cell_length_a                   19.8394(7)
_cell_length_b                   8.7672(3)
_cell_length_c                   13.8699(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.793(3)
_cell_angle_gamma                90
_cell_volume                     2361.57(15)
_cell_measurement_reflns_used    2469
_cell_measurement_theta_min      4.1890
_cell_measurement_theta_max      28.9107
_cell_oxdiff_length_a            19.8373(11)
_cell_oxdiff_length_b            8.7658(5)
_cell_oxdiff_length_c            13.8731(8)
_cell_oxdiff_angle_alpha         89.985(4)
_cell_oxdiff_angle_beta          101.813(5)
_cell_oxdiff_angle_gamma         89.973(4)
_cell_oxdiff_volume              2361.3(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C29 H29 N O5'
_chemical_formula_moiety         'C29 H29 N O5'
_chemical_compound_source        ?
_chemical_formula_weight         471.53


_cell_measurement_temperature    175

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.120
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.250
_exptl_absorpt_correction_T_min  0.97501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.090
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.79
_montpellier_reflns_completeness_maxres 99.18
_montpellier_reflns_redundancy_maxres 2.49

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.67 3.5 61.68 0.015 94.9 94.93
1 1.67 1.32 3.2 20.11 0.034 100.0 97.40
2 1.32 1.15 2.9 16.70 0.039 100.0 98.25
3 1.15 1.05 2.6 10.95 0.053 100.0 98.68
4 1.05 0.97 2.4 7.53 0.107 100.0 98.94
5 0.97 0.91 2.2 4.71 0.139 100.0 99.12
6 0.91 0.87 2.0 3.35 0.181 100.0 99.24
7 0.87 0.83 1.9 2.75 0.220 100.0 99.34
8 0.83 0.79 1.8 2.23 0.287 98.0 99.18
9 0.79 0.73 1.3 1.83 0.675 41.5 87.06
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      0.0183651000
_diffrn_orient_matrix_UB_12      -0.0608107000
_diffrn_orient_matrix_UB_13      -0.0164774000
_diffrn_orient_matrix_UB_21      0.0184821000
_diffrn_orient_matrix_UB_22      -0.0117852000
_diffrn_orient_matrix_UB_23      0.0488825000
_diffrn_orient_matrix_UB_31      -0.0256037000
_diffrn_orient_matrix_UB_32      -0.0520636000
_diffrn_orient_matrix_UB_33      0.0082099000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   16.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7849  -61.0000  155.0000 62

#__ type_ start__ end____ width___ exp.time_
  2 omega   37.00   74.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7849  179.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega   47.00   84.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7849  179.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega  -52.00   50.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7849    0.0000    0.0000 102

#__ type_ start__ end____ width___ exp.time_
  5 omega   34.00   59.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       17.7849  179.0000   30.0000 25

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            13155
_reflns_number_total             5448
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_unetI/netI     0.1100
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 5448
# Theoretical number of reflections is about 12282


_diffrn_reflns_theta_min         4.197
_diffrn_reflns_theta_max         29.005
_diffrn_measured_fraction_theta_max 0.869

_diffrn_reflns_theta_full        25.234
_diffrn_measured_fraction_theta_full 0.953


_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -25
_reflns_limit_h_max              25
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.21
_oxford_diffrn_Wilson_scale      0.13

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.45
_refine_diff_density_max         0.60


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     0
_refine_ls_number_parameters     335
_oxford_refine_ls_R_factor_ref   0.0714
_refine_ls_wR_factor_ref         0.0600
_refine_ls_goodness_of_fit_ref   1.1188
_refine_ls_shift/su_max          0.0003196
_refine_ls_shift/su_mean         0.0000423


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5448
_refine_ls_R_factor_all          0.1132
_refine_ls_wR_factor_all         0.0770

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3524
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_gt          0.0600

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 19.1 16.6 17.5 7.09 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.15784(8) 0.40325(18) 0.05993(12) 0.0427 1.0000 Uani . . . . . .
C2 C 0.19661(9) 0.3772(2) 0.15178(15) 0.0317 1.0000 Uani . . . . . .
C3 C 0.22716(10) 0.2403(2) 0.18374(15) 0.0314 1.0000 Uani . . . . . .
C4 C 0.26954(10) 0.2302(2) 0.27756(15) 0.0329 1.0000 Uani . . . . . .
N5 N 0.30062(8) 0.0880(2) 0.30637(13) 0.0355 1.0000 Uani . . . . . .
C6 C 0.36471(10) 0.0886(2) 0.34446(14) 0.0327 1.0000 Uani . . . . . .
C7 C 0.40554(10) -0.0452(2) 0.38491(14) 0.0313 1.0000 Uani . . . . . .
C8 C 0.47319(10) -0.0593(2) 0.36671(13) 0.0302 1.0000 Uani . . . . . .
C9 C 0.51760(11) -0.1770(2) 0.41458(14) 0.0335 1.0000 Uani . . . . . .
C10 C 0.58600(11) -0.1864(3) 0.39620(16) 0.0411 1.0000 Uani . . . . . .
C11 C 0.60864(11) -0.0858(3) 0.33597(17) 0.0420 1.0000 Uani . . . . . .
C12 C 0.56458(11) 0.0281(3) 0.28751(16) 0.0414 1.0000 Uani . . . . . .
C13 C 0.49906(11) 0.0423(3) 0.30207(15) 0.0373 1.0000 Uani . . . . . .
C14 C 0.49294(12) -0.2777(3) 0.47676(16) 0.0391 1.0000 Uani . . . . . .
C15 C 0.42651(12) -0.2676(2) 0.49460(16) 0.0375 1.0000 Uani . . . . . .
C16 C 0.38138(11) -0.1509(2) 0.44788(15) 0.0329 1.0000 Uani . . . . . .
C17 C 0.31423(11) -0.1415(3) 0.47137(16) 0.0396 1.0000 Uani . . . . . .
C18 C 0.29483(13) -0.2424(3) 0.53514(18) 0.0476 1.0000 Uani . . . . . .
C19 C 0.33936(14) -0.3561(3) 0.57997(19) 0.0530 1.0000 Uani . . . . . .
C20 C 0.40286(14) -0.3695(3) 0.56158(18) 0.0481 1.0000 Uani . . . . . .
C21 C 0.27882(11) 0.3574(3) 0.33801(16) 0.0384 1.0000 Uani . . . . . .
C22 C 0.24609(11) 0.4943(3) 0.30654(17) 0.0412 1.0000 Uani . . . . . .
C23 C 0.20500(10) 0.5053(2) 0.21414(16) 0.0358 1.0000 Uani . . . . . .
O24 O 0.16935(8) 0.63079(17) 0.17540(14) 0.0487 1.0000 Uani . . . . . .
C25 C 0.18158(13) 0.7741(3) 0.2252(2) 0.0485 1.0000 Uani . . . . . .
C26 C 0.13308(15) 0.8863(3) 0.1667(3) 0.0619 1.0000 Uani . . . . . .
O27 O 0.14618(10) 0.9111(2) 0.07257(15) 0.0613 1.0000 Uani . . . . . .
O30 O 0.05451(14) 0.7126(2) -0.13873(15) 0.0767 1.0000 Uani . . . . . .
C31 C -0.00623(16) 0.6219(4) -0.1444(2) 0.0711 1.0000 Uani . . . . . .
C32 C 0.00480(13) 0.4632(4) -0.17572(19) 0.0547 1.0000 Uani . . . . . .
O33 O 0.04465(8) 0.3765(2) -0.09841(12) 0.0509 1.0000 Uani . . . . . .
C34 C 0.11323(14) 0.3482(4) -0.10563(18) 0.0591 1.0000 Uani . . . . . .
C35 C 0.15162(14) 0.2845(3) -0.00975(17) 0.0487 1.0000 Uani . . . . . .
H31 H 0.2206 0.1546 0.1430 0.0374 1.0000 Uiso R . . . . .
H61 H 0.3885 0.1826 0.3477 0.0378 1.0000 Uiso R . . . . .
H101 H 0.6152 -0.2630 0.4269 0.0476 1.0000 Uiso R . . . . .
H111 H 0.6538 -0.0920 0.3271 0.0492 1.0000 Uiso R . . . . .
H121 H 0.5802 0.0948 0.2446 0.0497 1.0000 Uiso R . . . . .
H131 H 0.4706 0.1206 0.2693 0.0442 1.0000 Uiso R . . . . .
H141 H 0.5224 -0.3561 0.5071 0.0464 1.0000 Uiso R . . . . .
H171 H 0.2833 -0.0657 0.4419 0.0469 1.0000 Uiso R . . . . .
H181 H 0.2508 -0.2341 0.5488 0.0568 1.0000 Uiso R . . . . .
H191 H 0.3249 -0.4234 0.6232 0.0641 1.0000 Uiso R . . . . .
H201 H 0.4332 -0.4453 0.5930 0.0568 1.0000 Uiso R . . . . .
H211 H 0.3070 0.3517 0.4009 0.0462 1.0000 Uiso R . . . . .
H221 H 0.2525 0.5779 0.3492 0.0483 1.0000 Uiso R . . . . .
H251 H 0.2287 0.8058 0.2276 0.0570 1.0000 Uiso R . . . . .
H252 H 0.1724 0.7672 0.2912 0.0573 1.0000 Uiso R . . . . .
H261 H 0.1378 0.9843 0.2007 0.0750 1.0000 Uiso R . . . . .
H262 H 0.0865 0.8489 0.1606 0.0751 1.0000 Uiso R . . . . .
H311 H -0.0427 0.6680 -0.1928 0.0810 1.0000 Uiso R . . . . .
H312 H -0.0191 0.6207 -0.0805 0.0812 1.0000 Uiso R . . . . .
H321 H 0.0279 0.4666 -0.2310 0.0641 1.0000 Uiso R . . . . .
H322 H -0.0394 0.4135 -0.1951 0.0640 1.0000 Uiso R . . . . .
H341 H 0.1343 0.4445 -0.1189 0.0692 1.0000 Uiso R . . . . .
H342 H 0.1153 0.2762 -0.1588 0.0695 1.0000 Uiso R . . . . .
H351 H 0.1970 0.2486 -0.0169 0.0567 1.0000 Uiso R . . . . .
H352 H 0.1263 0.2009 0.0109 0.0566 1.0000 Uiso R . . . . .
C28 C 0.0995(3) 0.8864(6) -0.0204(5) 0.0554 0.634(9) Uani . U P 1 1 .
C29 C 0.0882(3) 0.7215(6) -0.0454(4) 0.0704 0.634(9) Uani . . P 1 1 .
C281 C 0.0941(4) 0.7987(11) 0.0275(7) 0.0636 0.366(9) Uani . U P 1 2 .
C291 C 0.0773(4) 0.8473(9) -0.0772(7) 0.0485 0.366(9) Uani . . P 1 2 .
H281 H 0.1180 0.9335 -0.0710 0.0680 0.634(9) Uiso R . P 1 1 .
H282 H 0.0563 0.9316 -0.0180 0.0680 0.634(9) Uiso R . P 1 1 .
H291 H 0.1313 0.6708 -0.0376 0.0983 0.634(9) Uiso R . P 1 1 .
H292 H 0.0617 0.6762 -0.0031 0.0983 0.634(9) Uiso R . P 1 1 .
H2811 H 0.0547 0.8039 0.0566 0.0680 0.366(9) Uiso R . P 1 2 .
H2812 H 0.1120 0.6979 0.0336 0.0680 0.366(9) Uiso R . P 1 2 .
H2911 H 0.1170 0.8907 -0.0949 0.0576 0.366(9) Uiso R . P 1 2 .
H2912 H 0.0413 0.9205 -0.0866 0.0576 0.366(9) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.173(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.366(2) yes
O1 . C35 . 1.409(3) yes
C2 . C3 . 1.377(3) yes
C2 . C23 . 1.406(3) yes
C3 . C4 . 1.400(3) yes
C3 . H31 . 0.933 no
C4 . N5 . 1.412(3) yes
C4 . C21 . 1.385(3) yes
N5 . C6 . 1.273(3) yes
C6 . C7 . 1.470(3) yes
C6 . H61 . 0.947 no
C7 . C8 . 1.421(3) yes
C7 . C16 . 1.422(3) yes
C8 . C9 . 1.429(3) yes
C8 . C13 . 1.431(3) yes
C9 . C10 . 1.433(3) yes
C9 . C14 . 1.391(3) yes
C10 . C11 . 1.353(3) yes
C10 . H101 . 0.932 no
C11 . C12 . 1.404(3) yes
C11 . H111 . 0.930 no
C12 . C13 . 1.361(3) yes
C12 . H121 . 0.931 no
C13 . H131 . 0.944 no
C14 . C15 . 1.393(3) yes
C14 . H141 . 0.944 no
C15 . C16 . 1.425(3) yes
C15 . C20 . 1.435(3) yes
C16 . C17 . 1.437(3) yes
C17 . C18 . 1.361(3) yes
C17 . H171 . 0.940 no
C18 . C19 . 1.392(4) yes
C18 . H181 . 0.934 no
C19 . C20 . 1.341(4) yes
C19 . H191 . 0.928 no
C20 . H201 . 0.942 no
C21 . C22 . 1.392(3) yes
C21 . H211 . 0.937 no
C22 . C23 . 1.374(3) yes
C22 . H221 . 0.934 no
C23 . O24 . 1.358(3) yes
O24 . C25 . 1.430(3) yes
C25 . C26 . 1.494(4) yes
C25 . H251 . 0.970 no
C25 . H252 . 0.971 no
C26 . O27 . 1.399(4) yes
C26 . H261 . 0.976 no
C26 . H262 . 0.968 no
O27 . C28 . 1.443(7) yes
O27 . C281 . 1.472(8) yes
O30 . C31 . 1.432(4) yes
O30 . C29 . 1.333(5) yes
O30 . C31 . 1.432(4) yes
O30 . C291 . 1.473(10) yes
C31 . C32 . 1.487(5) yes
C31 . H311 . 0.969 no
C31 . H312 . 0.972 no
C32 . O33 . 1.416(3) yes
C32 . H321 . 0.971 no
C32 . H322 . 0.967 no
O33 . C34 . 1.407(3) yes
C34 . C35 . 1.499(3) yes
C34 . H341 . 0.976 no
C34 . H342 . 0.978 no
C35 . H351 . 0.977 no
C35 . H352 . 0.965 no
C28 . C29 . 1.493(8) yes
C28 . H281 . 0.950 no
C28 . H282 . 0.950 no
C29 . H291 . 0.950 no
C29 . H292 . 0.950 no
C281 . C291 . 1.484(14) yes
C281 . H2811 . 0.950 no
C281 . H2812 . 0.950 no
C291 . H2911 . 0.950 no
C291 . H2912 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C35 . 118.04(17) yes
O1 . C2 . C3 . 124.95(19) yes
O1 . C2 . C23 . 114.44(18) yes
C3 . C2 . C23 . 120.60(19) yes
C2 . C3 . C4 . 119.74(19) yes
C2 . C3 . H31 . 120.6 no
C4 . C3 . H31 . 119.6 no
C3 . C4 . N5 . 117.64(19) yes
C3 . C4 . C21 . 119.4(2) yes
N5 . C4 . C21 . 122.91(18) yes
C4 . N5 . C6 . 117.09(18) yes
N5 . C6 . C7 . 125.50(19) yes
N5 . C6 . H61 . 118.0 no
C7 . C6 . H61 . 116.5 no
C6 . C7 . C8 . 117.92(18) yes
C6 . C7 . C16 . 121.72(18) yes
C8 . C7 . C16 . 120.12(18) yes
C7 . C8 . C9 . 119.69(18) yes
C7 . C8 . C13 . 121.99(18) yes
C9 . C8 . C13 . 118.32(18) yes
C8 . C9 . C10 . 118.37(19) yes
C8 . C9 . C14 . 118.98(19) yes
C10 . C9 . C14 . 122.6(2) yes
C9 . C10 . C11 . 121.2(2) yes
C9 . C10 . H101 . 118.9 no
C11 . C10 . H101 . 119.9 no
C10 . C11 . C12 . 120.4(2) yes
C10 . C11 . H111 . 119.6 no
C12 . C11 . H111 . 120.0 no
C11 . C12 . C13 . 120.9(2) yes
C11 . C12 . H121 . 119.8 no
C13 . C12 . H121 . 119.3 no
C8 . C13 . C12 . 120.8(2) yes
C8 . C13 . H131 . 119.9 no
C12 . C13 . H131 . 119.4 no
C9 . C14 . C15 . 122.4(2) yes
C9 . C14 . H141 . 118.3 no
C15 . C14 . H141 . 119.3 no
C14 . C15 . C16 . 119.63(19) yes
C14 . C15 . C20 . 121.5(2) yes
C16 . C15 . C20 . 118.9(2) yes
C15 . C16 . C7 . 119.18(19) yes
C15 . C16 . C17 . 117.61(19) yes
C7 . C16 . C17 . 123.13(19) yes
C16 . C17 . C18 . 120.6(2) yes
C16 . C17 . H171 . 119.7 no
C18 . C17 . H171 . 119.7 no
C17 . C18 . C19 . 121.2(2) yes
C17 . C18 . H181 . 118.9 no
C19 . C18 . H181 . 119.9 no
C18 . C19 . C20 . 120.9(2) yes
C18 . C19 . H191 . 119.5 no
C20 . C19 . H191 . 119.6 no
C15 . C20 . C19 . 120.9(2) yes
C15 . C20 . H201 . 118.4 no
C19 . C20 . H201 . 120.7 no
C4 . C21 . C22 . 120.59(19) yes
C4 . C21 . H211 . 120.1 no
C22 . C21 . H211 . 119.3 no
C21 . C22 . C23 . 120.2(2) yes
C21 . C22 . H221 . 118.9 no
C23 . C22 . H221 . 120.9 no
C2 . C23 . C22 . 119.4(2) yes
C2 . C23 . O24 . 114.64(18) yes
C22 . C23 . O24 . 126.0(2) yes
C23 . O24 . C25 . 119.83(18) yes
O24 . C25 . C26 . 106.8(2) yes
O24 . C25 . H251 . 109.6 no
C26 . C25 . H251 . 109.8 no
O24 . C25 . H252 . 110.8 no
C26 . C25 . H252 . 109.3 no
H251 . C25 . H252 . 110.5 no
C25 . C26 . O27 . 112.8(2) yes
C25 . C26 . H261 . 109.3 no
O27 . C26 . H261 . 107.3 no
C25 . C26 . H262 . 108.8 no
O27 . C26 . H262 . 109.1 no
H261 . C26 . H262 . 109.6 no
C26 . O27 . C28 . 127.1(3) yes
C26 . O27 . C281 . 92.5(4) yes
C31 . O30 . C29 . 109.6(3) yes
C31 . O30 . C291 . 129.2(4) yes
O30 . C31 . C32 . 111.3(2) yes
O30 . C31 . H311 . 108.0 no
C32 . C31 . H311 . 108.8 no
O30 . C31 . H312 . 109.3 no
C32 . C31 . H312 . 109.7 no
H311 . C31 . H312 . 109.8 no
C31 . C32 . O33 . 112.0(2) yes
C31 . C32 . H321 . 108.8 no
O33 . C32 . H321 . 109.5 no
C31 . C32 . H322 . 108.9 no
O33 . C32 . H322 . 107.7 no
H321 . C32 . H322 . 110.0 no
C32 . O33 . C34 . 116.0(2) yes
O33 . C34 . C35 . 109.0(2) yes
O33 . C34 . H341 . 108.5 no
C35 . C34 . H341 . 109.3 no
O33 . C34 . H342 . 111.0 no
C35 . C34 . H342 . 109.6 no
H341 . C34 . H342 . 109.3 no
C34 . C35 . O1 . 106.9(2) yes
C34 . C35 . H351 . 109.9 no
O1 . C35 . H351 . 110.8 no
C34 . C35 . H352 . 110.2 no
O1 . C35 . H352 . 109.6 no
H351 . C35 . H352 . 109.4 no
O27 . C28 . C29 . 113.0(4) yes
O27 . C28 . H281 . 108.6 no
C29 . C28 . H281 . 108.2 no
O27 . C28 . H282 . 108.9 no
C29 . C28 . H282 . 108.6 no
H281 . C28 . H282 . 109.5 no
C28 . C29 . O30 . 107.7(4) yes
C28 . C29 . H291 . 109.8 no
O30 . C29 . H291 . 110.1 no
C28 . C29 . H292 . 109.7 no
O30 . C29 . H292 . 110.1 no
H291 . C29 . H292 . 109.5 no
O27 . C281 . C291 . 102.7(7) yes
O27 . C281 . H2811 . 110.7 no
C291 . C281 . H2811 . 111.3 no
O27 . C281 . H2812 . 111.5 no
C291 . C281 . H2812 . 111.1 no
H2811 . C281 . H2812 . 109.5 no
C281 . C291 . O30 . 108.5(6) yes
C281 . C291 . H2911 . 109.6 no
O30 . C291 . H2911 . 110.1 no
C281 . C291 . H2912 . 109.9 no
O30 . C291 . H2912 . 109.2 no
H2911 . C291 . H2912 . 109.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C17 . H171 . N5 . 123.60(7) 0.940 2.394 3.018(4) yes
C29 . H2812 . O24 . 170.7(8) 1.120 2.143 3.253(4) yes
C29 . H2812 . C26 . 125.9(7) 1.120 2.448 3.234(4) yes


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1058508'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_exptl_special_details           
;
 The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
_cell_length_a                   7.6600(6)
_cell_length_b                   8.1559(6)
_cell_length_c                   20.1223(13)
_cell_angle_alpha                91.773(5)
_cell_angle_beta                 94.378(6)
_cell_angle_gamma                112.400(7)
_cell_volume                     1156.41(15)
_cell_measurement_reflns_used    2360
_cell_measurement_theta_min      4.2031
_cell_measurement_theta_max      32.4254
_cell_oxdiff_length_a            7.6600(6)
_cell_oxdiff_length_b            8.1559(6)
_cell_oxdiff_length_c            20.1223(13)
_cell_oxdiff_angle_alpha         91.773(5)
_cell_oxdiff_angle_beta          94.378(6)
_cell_oxdiff_angle_gamma         112.400(7)
_cell_oxdiff_volume              1156.41(14)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C31 H31 N'
_chemical_formula_moiety         'C31 H31 N'
_chemical_compound_source        ?
_chemical_formula_weight         417.57


_cell_measurement_temperature    2175

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_max          0.400
_exptl_absorpt_correction_T_min  0.99206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.068
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 16.0143

_diffrn_measurement_device       Serial
_diffrn_radiation_wavelength     0.71073
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.66
_montpellier_reflns_completeness_maxres 87.59
_montpellier_reflns_redundancy_maxres 1.71

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 1.47 2.3 33.57 0.013 97.1 97.09
1 1.47 1.18 2.2 19.80 0.018 100.0 98.52
2 1.18 1.03 2.0 15.12 0.023 100.0 99.01
3 1.03 0.94 1.8 8.94 0.042 100.0 99.26
4 0.94 0.87 1.7 6.68 0.062 99.3 99.27
5 0.87 0.82 1.6 5.39 0.082 98.8 99.19
6 0.82 0.78 1.5 4.90 0.085 98.0 99.02
7 0.78 0.74 1.4 4.46 0.088 97.6 98.84
8 0.74 0.71 1.3 3.87 0.095 96.2 98.54
9 0.71 0.66 1.2 3.35 0.101 44.1 87.59
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      0.0721878000
_diffrn_orient_matrix_UB_12      -0.0104544000
_diffrn_orient_matrix_UB_13      -0.0176435000
_diffrn_orient_matrix_UB_21      -0.0670122000
_diffrn_orient_matrix_UB_22      -0.0397207000
_diffrn_orient_matrix_UB_23      -0.0279716000
_diffrn_orient_matrix_UB_31      0.0205303000
_diffrn_orient_matrix_UB_32      0.0848471000
_diffrn_orient_matrix_UB_33      -0.0127054000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   61.00   87.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.1131   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00   95.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.1131   77.0000  -30.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   54.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.1131  -77.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega    5.00   94.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.1131   77.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  5 omega    4.00   47.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.1131   77.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
  6 omega  -63.00  -34.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.8944   96.0000  176.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega  -57.00    0.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.8944    0.0000  150.0000 57

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      175
_diffrn_reflns_number            12532
_reflns_number_total             7349
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_unetI/netI     0.1200
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 7349
# Theoretical number of reflections is about 16741


_diffrn_reflns_theta_min         4.212
_diffrn_reflns_theta_max         32.499
_diffrn_measured_fraction_theta_max 0.876

_diffrn_reflns_theta_full        25.024
_diffrn_measured_fraction_theta_full 0.986


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_reflns_limit_h_min              -11
_reflns_limit_h_max              10
_reflns_limit_k_min              -12
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              30

_oxford_diffrn_Wilson_B_factor   1.57
_oxford_diffrn_Wilson_scale      0.19

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.31
_refine_diff_density_max         0.39


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         4850
_refine_ls_number_restraints     0
_refine_ls_number_parameters     289
_oxford_refine_ls_R_factor_ref   0.0617
_refine_ls_wR_factor_ref         0.0630
_refine_ls_goodness_of_fit_ref   1.1063
_refine_ls_shift/su_max          0.0004428
_refine_ls_shift/su_mean         0.0000388


# The values computed with all filters except I/sigma
_oxford_reflns_number_all        7349
_refine_ls_R_factor_all          0.0974
_refine_ls_wR_factor_all         0.0817

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4850
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_gt          0.0630

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 8.06 3.27 6.67 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.48414(16) 0.21109(16) 0.42532(5) 0.0262 1.0000 Uani . . . . . .
C2 C 0.64407(19) 0.23497(17) 0.47091(6) 0.0235 1.0000 Uani . . . . . .
C3 C 0.67369(19) 0.34736(18) 0.52818(6) 0.0253 1.0000 Uani . . . . . .
C4 C 0.83158(19) 0.38233(18) 0.57344(6) 0.0249 1.0000 Uani . . . . . .
C5 C 0.96670(18) 0.31093(16) 0.56292(6) 0.0216 1.0000 Uani . . . . . .
C6 C 1.14164(19) 0.34625(17) 0.61078(6) 0.0238 1.0000 Uani . . . . . .
C7 C 1.17931(18) 0.48886(17) 0.66642(6) 0.0219 1.0000 Uani . . . . . .
C8 C 1.35660(18) 0.51997(17) 0.71340(6) 0.0226 1.0000 Uani . . . . . .
C9 C 1.39109(18) 0.67012(17) 0.76602(6) 0.0227 1.0000 Uani . . . . . .
C10 C 1.55819(18) 0.70448(17) 0.81810(6) 0.0230 1.0000 Uani . . . . . .
C11 C 1.58448(18) 0.85574(18) 0.86962(6) 0.0241 1.0000 Uani . . . . . .
C12 C 1.7478(2) 0.88863(19) 0.92324(7) 0.0282 1.0000 Uani . . . . . .
C13 C 1.7741(2) 1.0435(2) 0.97256(7) 0.0345 1.0000 Uani . . . . . .
H132 H 1.8789 1.0779 1.0034 0.0384 1.0000 Uiso R . . . . .
H133 H 1.6607 1.0163 0.9951 0.0386 1.0000 Uiso R . . . . .
H131 H 1.7877 1.1439 0.9469 0.0396 1.0000 Uiso R . . . . .
H122 H 1.7134 0.7831 0.9475 0.0272 1.0000 Uiso R . . . . .
H121 H 1.8650 0.9156 0.9016 0.0268 1.0000 Uiso R . . . . .
H112 H 1.4620 0.8222 0.8884 0.0198 1.0000 Uiso R . . . . .
H111 H 1.6052 0.9625 0.8450 0.0208 1.0000 Uiso R . . . . .
H101 H 1.5349 0.5945 0.8398 0.0190 1.0000 Uiso R . . . . .
H102 H 1.6685 0.7348 0.7954 0.0194 1.0000 Uiso R . . . . .
H91 H 1.2760 0.6463 0.7887 0.0182 1.0000 Uiso R . . . . .
H92 H 1.4158 0.7825 0.7433 0.0172 1.0000 Uiso R . . . . .
H81 H 1.3431 0.4136 0.7355 0.0186 1.0000 Uiso R . . . . .
H82 H 1.4624 0.5506 0.6873 0.0187 1.0000 Uiso R . . . . .
H71 H 1.0718 0.4472 0.6938 0.0194 1.0000 Uiso R . . . . .
H72 H 1.1990 0.6039 0.6473 0.0181 1.0000 Uiso R . . . . .
H61 H 1.1254 0.2378 0.6323 0.0208 1.0000 Uiso R . . . . .
H62 H 1.2527 0.3803 0.5836 0.0211 1.0000 Uiso R . . . . .
C14 C 0.93806(19) 0.20277(18) 0.50472(6) 0.0252 1.0000 Uani . . . . . .
C15 C 0.7801(2) 0.16433(18) 0.45957(6) 0.0261 1.0000 Uani . . . . . .
H151 H 0.7699 0.0965 0.4222 0.0233 1.0000 Uiso R . . . . .
H141 H 1.0279 0.1586 0.4966 0.0217 1.0000 Uiso R . . . . .
H41 H 0.8523 0.4554 0.6116 0.0233 1.0000 Uiso R . . . . .
H31 H 0.5820 0.4005 0.5348 0.0228 1.0000 Uiso R . . . . .
C16 C 0.41341(19) 0.06900(18) 0.38680(7) 0.0259 1.0000 Uani . . . . . .
C17 C 0.25580(18) 0.03975(16) 0.33561(6) 0.0215 1.0000 Uani . . . . . .
C18 C 0.20972(17) -0.09387(16) 0.28330(6) 0.0200 1.0000 Uani . . . . . .
C19 C 0.05292(17) -0.11931(16) 0.23515(6) 0.0193 1.0000 Uani . . . . . .
C20 C -0.05340(18) -0.01081(17) 0.24002(6) 0.0217 1.0000 Uani . . . . . .
C21 C -0.0021(2) 0.12156(18) 0.29228(7) 0.0272 1.0000 Uani . . . . . .
C22 C 0.14909(19) 0.14554(17) 0.33872(6) 0.0255 1.0000 Uani . . . . . .
H221 H 0.1810 0.2358 0.3721 0.0266 1.0000 Uiso R . . . . .
H211 H -0.0741 0.1955 0.2963 0.0245 1.0000 Uiso R . . . . .
C23 C -0.2115(2) -0.04041(19) 0.19122(7) 0.0290 1.0000 Uani . . . . . .
C24 C -0.2604(2) -0.1690(2) 0.14144(7) 0.0296 1.0000 Uani . . . . . .
C25 C -0.15583(19) -0.28026(18) 0.13476(6) 0.0244 1.0000 Uani . . . . . .
C26 C 0.00112(17) -0.25399(16) 0.18196(6) 0.0207 1.0000 Uani . . . . . .
C27 C 0.10687(19) -0.36328(18) 0.17632(7) 0.0255 1.0000 Uani . . . . . .
C28 C 0.2651(2) -0.33313(19) 0.22441(7) 0.0292 1.0000 Uani . . . . . .
C29 C 0.31472(19) -0.20513(18) 0.27477(7) 0.0257 1.0000 Uani . . . . . .
H291 H 0.4154 -0.1930 0.3040 0.0240 1.0000 Uiso R . . . . .
H281 H 0.3346 -0.4065 0.2214 0.0262 1.0000 Uiso R . . . . .
C30 C 0.0525(2) -0.49669(19) 0.12436(7) 0.0336 1.0000 Uani . . . . . .
C31 C -0.1013(2) -0.5215(2) 0.07872(7) 0.0360 1.0000 Uani . . . . . .
C32 C -0.2044(2) -0.4149(2) 0.08363(7) 0.0311 1.0000 Uani . . . . . .
H321 H -0.3070 -0.4295 0.0547 0.0318 1.0000 Uiso R . . . . .
H311 H -0.1375 -0.6109 0.0449 0.0368 1.0000 Uiso R . . . . .
H301 H 0.1235 -0.5713 0.1220 0.0322 1.0000 Uiso R . . . . .
H241 H -0.3620 -0.1832 0.1120 0.0266 1.0000 Uiso R . . . . .
H231 H -0.2803 0.0315 0.1952 0.0261 1.0000 Uiso R . . . . .
H161 H 0.4629 -0.0209 0.3926 0.0218 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.942(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.4198(17) yes
N1 . C16 . 1.2803(17) yes
C2 . C3 . 1.3986(18) yes
C2 . C15 . 1.3985(19) yes
C3 . C4 . 1.3880(18) yes
C3 . H31 . 0.971 no
C4 . C5 . 1.3930(18) yes
C4 . H41 . 0.922 no
C5 . C6 . 1.5158(18) yes
C5 . C14 . 1.3954(17) yes
C6 . C7 . 1.5178(17) yes
C6 . H61 . 0.966 no
C6 . H62 . 1.000 no
C7 . C8 . 1.5262(17) yes
C7 . H71 . 0.982 no
C7 . H72 . 0.987 no
C8 . C9 . 1.5234(18) yes
C8 . H81 . 0.961 no
C8 . H82 . 0.955 no
C9 . C10 . 1.5227(16) yes
C9 . H91 . 0.979 no
C9 . H92 . 0.996 no
C10 . C11 . 1.5286(18) yes
C10 . H101 . 0.970 no
C10 . H102 . 0.944 no
C11 . C12 . 1.5238(17) yes
C11 . H112 . 0.981 no
C11 . H111 . 0.981 no
C12 . C13 . 1.523(2) yes
C12 . H122 . 0.960 no
C12 . H121 . 0.979 no
C13 . H132 . 0.922 no
C13 . H133 . 0.964 no
C13 . H131 . 0.958 no
C14 . C15 . 1.3830(18) yes
C14 . H141 . 0.912 no
C15 . H151 . 0.900 no
C16 . C17 . 1.4666(18) yes
C16 . H161 . 0.951 no
C17 . C18 . 1.4139(17) yes
C17 . C22 . 1.3995(18) yes
C18 . C19 . 1.4299(17) yes
C18 . C29 . 1.4378(18) yes
C19 . C20 . 1.4185(17) yes
C19 . C26 . 1.4281(16) yes
C20 . C21 . 1.4032(18) yes
C20 . C23 . 1.4388(18) yes
C21 . C22 . 1.3795(19) yes
C21 . H211 . 0.966 no
C22 . H221 . 0.927 no
C23 . C24 . 1.350(2) yes
C23 . H231 . 0.931 no
C24 . C25 . 1.4305(19) yes
C24 . H241 . 0.908 no
C25 . C26 . 1.4178(18) yes
C25 . C32 . 1.4013(19) yes
C26 . C27 . 1.4219(17) yes
C27 . C28 . 1.4301(19) yes
C27 . C30 . 1.4029(18) yes
C28 . C29 . 1.3545(19) yes
C28 . H281 . 0.944 no
C29 . H291 . 0.905 no
C30 . C31 . 1.383(2) yes
C30 . H301 . 0.961 no
C31 . C32 . 1.385(2) yes
C31 . H311 . 0.926 no
C32 . H321 . 0.908 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C16 . 118.64(12) yes
N1 . C2 . C3 . 117.35(12) yes
N1 . C2 . C15 . 124.09(12) yes
C3 . C2 . C15 . 118.37(12) yes
C2 . C3 . C4 . 120.32(13) yes
C2 . C3 . H31 . 118.1 no
C4 . C3 . H31 . 121.6 no
C3 . C4 . C5 . 121.66(12) yes
C3 . C4 . H41 . 121.3 no
C5 . C4 . H41 . 117.1 no
C4 . C5 . C6 . 123.45(11) yes
C4 . C5 . C14 . 117.45(12) yes
C6 . C5 . C14 . 119.10(12) yes
C5 . C6 . C7 . 115.60(11) yes
C5 . C6 . H61 . 107.8 no
C7 . C6 . H61 . 106.3 no
C5 . C6 . H62 . 107.2 no
C7 . C6 . H62 . 109.3 no
H61 . C6 . H62 . 110.6 no
C6 . C7 . C8 . 113.83(11) yes
C6 . C7 . H71 . 107.0 no
C8 . C7 . H71 . 106.3 no
C6 . C7 . H72 . 109.9 no
C8 . C7 . H72 . 106.1 no
H71 . C7 . H72 . 113.8 no
C7 . C8 . C9 . 111.13(11) yes
C7 . C8 . H81 . 110.0 no
C9 . C8 . H81 . 108.8 no
C7 . C8 . H82 . 108.1 no
C9 . C8 . H82 . 109.3 no
H81 . C8 . H82 . 109.5 no
C8 . C9 . C10 . 115.32(11) yes
C8 . C9 . H91 . 109.3 no
C10 . C9 . H91 . 109.1 no
C8 . C9 . H92 . 108.7 no
C10 . C9 . H92 . 107.0 no
H91 . C9 . H92 . 107.0 no
C9 . C10 . C11 . 112.75(11) yes
C9 . C10 . H101 . 107.0 no
C11 . C10 . H101 . 110.5 no
C9 . C10 . H102 . 107.5 no
C11 . C10 . H102 . 108.8 no
H101 . C10 . H102 . 110.2 no
C10 . C11 . C12 . 113.46(11) yes
C10 . C11 . H112 . 105.1 no
C12 . C11 . H112 . 112.2 no
C10 . C11 . H111 . 106.9 no
C12 . C11 . H111 . 110.6 no
H112 . C11 . H111 . 108.2 no
C11 . C12 . C13 . 112.19(12) yes
C11 . C12 . H122 . 106.0 no
C13 . C12 . H122 . 107.7 no
C11 . C12 . H121 . 108.7 no
C13 . C12 . H121 . 108.5 no
H122 . C12 . H121 . 113.8 no
C12 . C13 . H132 . 116.2 no
C12 . C13 . H133 . 109.0 no
H132 . C13 . H133 . 110.0 no
C12 . C13 . H131 . 106.9 no
H132 . C13 . H131 . 106.7 no
H133 . C13 . H131 . 107.7 no
C5 . C14 . C15 . 121.68(12) yes
C5 . C14 . H141 . 118.2 no
C15 . C14 . H141 . 120.1 no
C2 . C15 . C14 . 120.49(12) yes
C2 . C15 . H151 . 121.2 no
C14 . C15 . H151 . 118.2 no
N1 . C16 . C17 . 121.81(13) yes
N1 . C16 . H161 . 118.6 no
C17 . C16 . H161 . 119.5 no
C16 . C17 . C18 . 121.05(12) yes
C16 . C17 . C22 . 119.43(12) yes
C18 . C17 . C22 . 119.52(11) yes
C17 . C18 . C19 . 119.03(11) yes
C17 . C18 . C29 . 123.51(11) yes
C19 . C18 . C29 . 117.45(11) yes
C18 . C19 . C20 . 120.06(11) yes
C18 . C19 . C26 . 120.62(11) yes
C20 . C19 . C26 . 119.31(11) yes
C19 . C20 . C21 . 119.20(11) yes
C19 . C20 . C23 . 118.87(11) yes
C21 . C20 . C23 . 121.93(12) yes
C20 . C21 . C22 . 120.59(12) yes
C20 . C21 . H211 . 119.9 no
C22 . C21 . H211 . 119.5 no
C17 . C22 . C21 . 121.59(12) yes
C17 . C22 . H221 . 119.9 no
C21 . C22 . H221 . 118.5 no
C20 . C23 . C24 . 121.41(12) yes
C20 . C23 . H231 . 117.9 no
C24 . C23 . H231 . 120.7 no
C23 . C24 . C25 . 121.25(12) yes
C23 . C24 . H241 . 118.2 no
C25 . C24 . H241 . 120.6 no
C24 . C25 . C26 . 118.68(12) yes
C24 . C25 . C32 . 122.23(13) yes
C26 . C25 . C32 . 119.09(13) yes
C19 . C26 . C25 . 120.48(11) yes
C19 . C26 . C27 . 119.92(11) yes
C25 . C26 . C27 . 119.60(12) yes
C26 . C27 . C28 . 118.39(12) yes
C26 . C27 . C30 . 119.24(13) yes
C28 . C27 . C30 . 122.37(13) yes
C27 . C28 . C29 . 121.75(12) yes
C27 . C28 . H281 . 118.8 no
C29 . C28 . H281 . 119.4 no
C18 . C29 . C28 . 121.84(12) yes
C18 . C29 . H291 . 120.3 no
C28 . C29 . H291 . 117.8 no
C27 . C30 . C31 . 120.63(14) yes
C27 . C30 . H301 . 118.1 no
C31 . C30 . H301 . 121.2 no
C30 . C31 . C32 . 120.50(13) yes
C30 . C31 . H311 . 120.2 no
C32 . C31 . H311 . 119.3 no
C25 . C32 . C31 . 120.92(14) yes
C25 . C32 . H321 . 116.8 no
C31 . C32 . H321 . 122.2 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/10/13 at 10:51:16
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 112,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 133,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/10/13 at 10:51:16
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10
_database_code_depnum_ccdc_archive 'CCDC 1058509'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-06-10 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
?
;
#--------------------------------------------------------------- 
_cell_length_a                   20.210(4)
_cell_length_b                   4.7596(11)
_cell_length_c                   20.150(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.938(14)
_cell_angle_gamma                90
_cell_volume                     1938.0(3)
_cell_measurement_reflns_used    550
_cell_measurement_theta_min      4.3330
_cell_measurement_theta_max      69.9410
_cell_oxdiff_length_a            20.211(3)
_cell_oxdiff_length_b            4.7560(9)
_cell_oxdiff_length_c            20.164(4)
_cell_oxdiff_angle_alpha         90.056(16)
_cell_oxdiff_angle_beta          90.877(15)
_cell_oxdiff_angle_gamma         89.900(13)
_cell_oxdiff_volume              1938.0(6)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C27 H23 N'
_chemical_formula_moiety         'C27 H23 N'
_chemical_compound_source        ?
_chemical_formula_weight         361.46


_cell_measurement_temperature    293

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_max          0.120
_exptl_absorpt_correction_T_min  0.01413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             767.995
_exptl_absorpt_coefficient_mu    0.540
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_detector_area_resol_mean 8.0851

_diffrn_measurement_device       Area
_diffrn_radiation_wavelength     1.54184
#montpellier_reflns_maxres is minimum d (highest resolution)
#where <I/sigI> <= 2.0
#(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999)
_montpellier_reflns_maxres       0.96
_montpellier_reflns_completeness_maxres 75.89
_montpellier_reflns_redundancy_maxres 1.54

#montpellier_diffrn_reflns_class_completeness_shell is completeness in shell
#montpellier_diffrn_class_reflns_cumul_completeness is cumulative
#completeness to resolution of shell
#Note: completeness percentage takes into account the fact whether
#group is centrosymmetric or not
loop_
_montpellier_diffrn_reflns_class_number
_montpellier_diffrn_reflns_class_d_res_high
_montpellier_diffrn_reflns_class_d_res_low
_montpellier_diffrn_reflns_class_redundancy
_montpellier_diffrn_reflns_class_av_I/uI
_diffrn_reflns_class_av_R_eq
_montpellier_diffrn_reflns_class_completeness_shell
_montpellier_diffrn_reflns_class_cumul_completeness
0 100.0 2.03 1.9 19.86 0.015 88.5 88.54
1 2.03 1.55 1.3 9.67 0.029 83.1 85.76
2 1.55 1.35 1.1 3.62 0.095 83.1 84.87
3 1.35 1.21 1.7 4.75 0.098 80.6 83.75
4 1.21 1.12 1.8 4.46 0.123 85.6 84.12
5 1.12 1.03 1.6 3.33 0.129 61.9 79.37
6 1.03 0.96 1.4 2.67 0.128 60.1 75.89
7 0.96 0.91 1.3 1.51 0.422 60.2 73.50
8 0.91 0.86 1.3 1.32 0.486 57.2 71.24
9 0.86 0.82 1.1 1.34 0.401 49.0 68.07
#End reflection statistics
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_orient_matrix_UB_11      0.0575866000
_diffrn_orient_matrix_UB_12      -0.1372573000
_diffrn_orient_matrix_UB_13      0.0391234000
_diffrn_orient_matrix_UB_21      0.0284821000
_diffrn_orient_matrix_UB_22      0.2931581000
_diffrn_orient_matrix_UB_23      0.0158117000
_diffrn_orient_matrix_UB_31      -0.0410377000
_diffrn_orient_matrix_UB_32      0.0119015000
_diffrn_orient_matrix_UB_33      0.0637022000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00    7.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00    5.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   26.00   68.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega   24.00  120.00   1.0000  157.9500
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 96

#__ type_ start__ end____ width___ exp.time_
  5 omega   72.00  110.00   1.0000  157.9500
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega  -11.00   20.00   1.0000  157.9500
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   26.00   61.00   1.0000  157.9500
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega   46.00   96.00   1.0000  157.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega   42.00   92.00   1.0000  157.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
 10 omega  102.00  174.00   1.0000  157.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 72

#__ type_ start__ end____ width___ exp.time_
 11 omega  109.00  167.00   1.0000  157.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   50.00   75.00   1.0000  157.9500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 25

;
_diffrn_measurement_method       'ω scans'

_diffrn_ambient_temperature      293
_diffrn_reflns_number            3825
_reflns_number_total             2599
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_unetI/netI     0.0710
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2599 
# Theoretical number of reflections is about 7467 


_diffrn_reflns_theta_min         4.376
_diffrn_reflns_theta_max         70.841
_diffrn_measured_fraction_theta_max 0.696

_diffrn_reflns_theta_full        25.100
_diffrn_measured_fraction_theta_full 0.905


_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -20
_reflns_limit_h_max              22
_reflns_limit_k_min              0
_reflns_limit_k_max              5
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     iterative #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.36
_refine_diff_density_max         0.36


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         1306
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_oxford_refine_ls_R_factor_ref   0.0918
_refine_ls_wR_factor_ref         0.0952
_refine_ls_goodness_of_fit_ref   1.0365
_refine_ls_shift/su_max          0.0001689
_refine_ls_shift/su_mean         0.0000319


# The values computed with all filters except I/sigma
_oxford_reflns_number_all        2599
_refine_ls_R_factor_all          0.1535
_refine_ls_wR_factor_all         0.1505

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1306
_refine_ls_R_factor_gt           0.0918
_refine_ls_wR_factor_gt          0.0952

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 23.2 13.5 18.4 7.31 -0.308 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.7492(3) -0.1604(11) 0.5357(3) 0.0726 1.0000 Uani . . . . . .
C2 C 0.7430(3) -0.0586(13) 0.4801(3) 0.0674 1.0000 Uani . . . . . .
C3 C 0.6922(3) 0.1604(11) 0.4631(3) 0.0490 1.0000 Uani . . . . . .
C4 C 0.6882(3) 0.2672(11) 0.3984(2) 0.0435 1.0000 Uani . . . . . .
C5 C 0.6399(3) 0.4728(11) 0.3821(2) 0.0437 1.0000 Uani . . . . . .
C6 C 0.5956(3) 0.5697(12) 0.4317(3) 0.0503 1.0000 Uani . . . . . .
C7 C 0.5480(3) 0.7816(12) 0.4135(3) 0.0591 1.0000 Uani . . . . . .
C8 C 0.5440(3) 0.8789(14) 0.3512(3) 0.0645 1.0000 Uani . . . . . .
C9 C 0.5867(3) 0.7897(13) 0.3013(3) 0.0568 1.0000 Uani . . . . . .
C10 C 0.6344(3) 0.5845(12) 0.3169(3) 0.0470 1.0000 Uani . . . . . .
C11 C 0.6773(3) 0.4931(12) 0.2673(3) 0.0516 1.0000 Uani . . . . . .
C12 C 0.6710(3) 0.6020(14) 0.2027(3) 0.0684 1.0000 Uani . . . . . .
C13 C 0.6241(4) 0.8039(15) 0.1883(3) 0.0812 1.0000 Uani . . . . . .
C14 C 0.5827(3) 0.8961(15) 0.2363(4) 0.0710 1.0000 Uani . . . . . .
H141 H 0.5515 1.0347 0.2264 0.0831 1.0000 Uiso R . . . . .
H131 H 0.6206 0.8750 0.1452 0.0971 1.0000 Uiso R . . . . .
H121 H 0.6991 0.5366 0.1702 0.0817 1.0000 Uiso R . . . . .
C15 C 0.7259(3) 0.2889(13) 0.2838(3) 0.0628 1.0000 Uani . . . . . .
C16 C 0.7312(3) 0.1821(12) 0.3460(3) 0.0570 1.0000 Uani . . . . . .
H161 H 0.7639 0.0478 0.3555 0.0673 1.0000 Uiso R . . . . .
H151 H 0.7549 0.2299 0.2512 0.0728 1.0000 Uiso R . . . . .
H81 H 0.5120 1.0102 0.3405 0.0743 1.0000 Uiso R . . . . .
H71 H 0.5192 0.8510 0.4462 0.0699 1.0000 Uiso R . . . . .
C17 C 0.6020(3) 0.4544(12) 0.4952(3) 0.0566 1.0000 Uani . . . . . .
C18 C 0.6484(3) 0.2524(13) 0.5097(3) 0.0588 1.0000 Uani . . . . . .
H181 H 0.6500 0.1733 0.5529 0.0700 1.0000 Uiso R . . . . .
H171 H 0.5749 0.5177 0.5283 0.0654 1.0000 Uiso R . . . . .
H21 H 0.7715 -0.1233 0.4475 0.0831 1.0000 Uiso R . . . . .
C19 C 0.8019(3) -0.3631(13) 0.5484(3) 0.0604 1.0000 Uani . . . . . .
C20 C 0.8026(4) -0.4938(14) 0.6072(3) 0.0795 1.0000 Uani . . . . . .
C21 C 0.8517(4) -0.6804(15) 0.6230(3) 0.0777 1.0000 Uani . . . . . .
C22 C 0.9030(3) -0.7374(12) 0.5821(3) 0.0579 1.0000 Uani . . . . . .
C23 C 0.9015(3) -0.6089(16) 0.5218(3) 0.0821 1.0000 Uani . . . . . .
C24 C 0.8514(4) -0.4223(17) 0.5039(4) 0.0924 1.0000 Uani . . . . . .
H241 H 0.8516 -0.3358 0.4620 0.1123 1.0000 Uiso R . . . . .
H231 H 0.9357 -0.6437 0.4917 0.0956 1.0000 Uiso R . . . . .
C25 C 0.9593(3) -0.9244(14) 0.6039(3) 0.0754 1.0000 Uani . . . . . .
C26 C 1.0114(3) -0.7557(15) 0.6457(3) 0.0763 1.0000 Uani . . . . . .
C27 C 1.0686(3) -0.9224(17) 0.6699(3) 0.0884 1.0000 Uani . . . . . .
C28 C 1.1163(4) -0.7469(17) 0.7101(4) 0.1049 1.0000 Uani . . . . . .
H282 H 1.1525 -0.8575 0.7257 0.1540 1.0000 Uiso R . . . . .
H283 H 1.0951 -0.6644 0.7472 0.1539 1.0000 Uiso R . . . . .
H281 H 1.1324 -0.5967 0.6831 0.1540 1.0000 Uiso R . . . . .
H271 H 1.0515 -1.0729 0.6979 0.1043 1.0000 Uiso R . . . . .
H272 H 1.0910 -1.0049 0.6321 0.1041 1.0000 Uiso R . . . . .
H261 H 0.9889 -0.6817 0.6837 0.0923 1.0000 Uiso R . . . . .
H262 H 1.0282 -0.6020 0.6195 0.0924 1.0000 Uiso R . . . . .
H251 H 0.9425 -1.0820 0.6300 0.0920 1.0000 Uiso R . . . . .
H252 H 0.9804 -1.0012 0.5646 0.0923 1.0000 Uiso R . . . . .
H211 H 0.8502 -0.7748 0.6643 0.0933 1.0000 Uiso R . . . . .
H201 H 0.7688 -0.4567 0.6385 0.0951 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.24(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.225(7) yes
N1 . C19 . 1.458(8) yes
C2 . C3 . 1.499(8) yes
C2 . H21 . 0.932 no
C3 . C4 . 1.401(7) yes
C3 . C18 . 1.373(8) yes
C4 . C5 . 1.417(7) yes
C4 . C16 . 1.436(7) yes
C5 . C6 . 1.428(7) yes
C5 . C10 . 1.420(7) yes
C6 . C7 . 1.437(8) yes
C6 . C17 . 1.397(8) yes
C7 . C8 . 1.340(8) yes
C7 . H71 . 0.945 no
C8 . C9 . 1.401(9) yes
C8 . H81 . 0.922 no
C9 . C10 . 1.404(8) yes
C9 . C14 . 1.406(8) yes
C10 . C11 . 1.403(8) yes
C11 . C12 . 1.406(7) yes
C11 . C15 . 1.418(8) yes
C12 . C13 . 1.376(9) yes
C12 . H121 . 0.928 no
C13 . C14 . 1.362(9) yes
C13 . H131 . 0.934 no
C14 . H141 . 0.931 no
C15 . C16 . 1.353(8) yes
C15 . H151 . 0.932 no
C16 . H161 . 0.937 no
C17 . C18 . 1.371(7) yes
C17 . H171 . 0.920 no
C18 . H181 . 0.947 no
C19 . C20 . 1.338(9) yes
C19 . C24 . 1.384(9) yes
C20 . C21 . 1.366(8) yes
C20 . H201 . 0.953 no
C21 . C22 . 1.361(8) yes
C21 . H211 . 0.948 no
C22 . C23 . 1.361(8) yes
C22 . C25 . 1.505(8) yes
C23 . C24 . 1.391(8) yes
C23 . H231 . 0.940 no
C24 . H241 . 0.939 no
C25 . C26 . 1.561(8) yes
C25 . H251 . 0.981 no
C25 . H252 . 0.975 no
C26 . C27 . 1.477(8) yes
C26 . H261 . 0.964 no
C26 . H262 . 0.968 no
C27 . C28 . 1.502(9) yes
C27 . H271 . 0.978 no
C27 . H272 . 0.974 no
C28 . H282 . 0.951 no
C28 . H283 . 0.953 no
C28 . H281 . 0.958 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C19 . 119.1(7) yes
N1 . C2 . C3 . 122.9(7) yes
N1 . C2 . H21 . 117.3 no
C3 . C2 . H21 . 119.8 no
C2 . C3 . C4 . 119.6(6) yes
C2 . C3 . C18 . 120.8(5) yes
C4 . C3 . C18 . 119.6(5) yes
C3 . C4 . C5 . 119.6(5) yes
C3 . C4 . C16 . 123.8(5) yes
C5 . C4 . C16 . 116.6(5) yes
C4 . C5 . C6 . 120.0(5) yes
C4 . C5 . C10 . 121.0(5) yes
C6 . C5 . C10 . 119.1(5) yes
C5 . C6 . C7 . 118.3(5) yes
C5 . C6 . C17 . 117.6(5) yes
C7 . C6 . C17 . 124.1(6) yes
C6 . C7 . C8 . 120.7(6) yes
C6 . C7 . H71 . 119.0 no
C8 . C7 . H71 . 120.3 no
C7 . C8 . C9 . 122.6(6) yes
C7 . C8 . H81 . 118.9 no
C9 . C8 . H81 . 118.5 no
C8 . C9 . C10 . 118.6(6) yes
C8 . C9 . C14 . 122.1(7) yes
C10 . C9 . C14 . 119.3(7) yes
C5 . C10 . C9 . 120.7(6) yes
C5 . C10 . C11 . 120.3(5) yes
C9 . C10 . C11 . 119.1(5) yes
C10 . C11 . C12 . 119.9(6) yes
C10 . C11 . C15 . 118.6(5) yes
C12 . C11 . C15 . 121.5(6) yes
C11 . C12 . C13 . 120.2(7) yes
C11 . C12 . H121 . 118.8 no
C13 . C12 . H121 . 120.9 no
C12 . C13 . C14 . 120.4(6) yes
C12 . C13 . H131 . 119.3 no
C14 . C13 . H131 . 120.3 no
C9 . C14 . C13 . 121.2(7) yes
C9 . C14 . H141 . 118.9 no
C13 . C14 . H141 . 119.9 no
C11 . C15 . C16 . 121.2(6) yes
C11 . C15 . H151 . 118.8 no
C16 . C15 . H151 . 119.9 no
C4 . C16 . C15 . 122.3(6) yes
C4 . C16 . H161 . 118.3 no
C15 . C16 . H161 . 119.4 no
C6 . C17 . C18 . 121.6(6) yes
C6 . C17 . H171 . 119.2 no
C18 . C17 . H171 . 119.2 no
C3 . C18 . C17 . 121.6(5) yes
C3 . C18 . H181 . 119.2 no
C17 . C18 . H181 . 119.2 no
N1 . C19 . C20 . 117.4(7) yes
N1 . C19 . C24 . 123.7(6) yes
C20 . C19 . C24 . 118.9(6) yes
C19 . C20 . C21 . 120.3(7) yes
C19 . C20 . H201 . 120.2 no
C21 . C20 . H201 . 119.5 no
C20 . C21 . C22 . 123.2(6) yes
C20 . C21 . H211 . 118.6 no
C22 . C21 . H211 . 118.2 no
C21 . C22 . C23 . 116.4(6) yes
C21 . C22 . C25 . 121.5(6) yes
C23 . C22 . C25 . 122.1(6) yes
C22 . C23 . C24 . 121.6(7) yes
C22 . C23 . H231 . 119.4 no
C24 . C23 . H231 . 119.0 no
C23 . C24 . C19 . 119.5(6) yes
C23 . C24 . H241 . 120.0 no
C19 . C24 . H241 . 120.5 no
C22 . C25 . C26 . 110.7(5) yes
C22 . C25 . H251 . 110.0 no
C26 . C25 . H251 . 109.8 no
C22 . C25 . H252 . 108.9 no
C26 . C25 . H252 . 109.3 no
H251 . C25 . H252 . 108.0 no
C25 . C26 . C27 . 114.8(6) yes
C25 . C26 . H261 . 107.1 no
C27 . C26 . H261 . 108.2 no
C25 . C26 . H262 . 109.4 no
C27 . C26 . H262 . 107.9 no
H261 . C26 . H262 . 109.4 no
C26 . C27 . C28 . 111.7(6) yes
C26 . C27 . H271 . 107.6 no
C28 . C27 . H271 . 109.0 no
C26 . C27 . H272 . 109.3 no
C28 . C27 . H272 . 110.0 no
H271 . C27 . H272 . 109.2 no
C27 . C28 . H282 . 110.8 no
C27 . C28 . H283 . 111.1 no
H282 . C28 . H283 . 108.6 no
C27 . C28 . H281 . 109.3 no
H282 . C28 . H281 . 109.6 no
H283 . C28 . H281 . 107.4 no


# start Validation Reply Form
_vrf_REFNR01_1                   
;
PROBLEM: Ratio of reflections to parameters is < 6 for a
RESPONSE: tiny and weakly diffracting crystal. A measurement using
 a Gemini-S diffractometer yielded the structure but with a very high R-factor
 (35%). A remeasurement on a Supernova diffractometer yielded a much better
 R-factor, but the data remain weak.
;
_vrf_PLAT027_1                   
;
PROBLEM: _diffrn_reflns_theta_full (too) Low ............      25.10 Degree
RESPONSE: same reply as for _vrf_REFNR01_1
;
_vrf_PLAT029_1                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.905 Note
RESPONSE: same reply as for _vrf_REFNR01_1
;
# end Validation Reply For
